Nitrogen-containing heterocyclic compounds and medicinal use thereof

ABSTRACT

The compound represented by formulae (I) and (II), the salt thereof, the N-oxide thereof or the solvate thereof, or the prodrug thereof and the pharmaceutical composition comprising thereof have a CXCR4-regulating effect, and they are effective in treatment and prevention of various inflammatory disease, various allergic disease, acquired immunodeficiency syndrome infection with human immunodeficiency virus, or agents for regeneration therapy. 
     
       
         
         
             
             
         
       
     
     (wherein ring A represents a nitrogen-containing heterocyclic group which may have a substituent(s); ring B represents a homocyclic group which may have a substituent(s) or a heterocyclic group which may have a substituent(s); and Y represents a hydrocarbon group which may have a substituent(s), a heterocyclic group which may have a substituent(s), an amino group which may be protected, a hydroxyl group which may be protected or a mercapto group which may be protected; T represents ring A or an amino group which may be protected.)

CROSS REFERENCE TO THE RELATED APPLICATIONS

This is a Continuation of application Ser. No. 12/776,989 filed May 10,2010 which is a Continuation of application Ser. No. 10/538,758 filedJun. 10, 2005, now U.S. Pat. No. 7,759,336 issued Jul. 20, 2010, whichis the National Stage of Entry of PCT/JP03/15718, filed on Dec. 9, 2003,which claims priority from Japanese Patent Application Nos. 2002-357446and 2003-162706 filed on Dec. 10, 2002 and Jun. 6, 2003, respectively.The entire disclosures of the prior applications are hereby incorporatedby reference.

TECHNICAL FIELD

The present invention relates to CXCR4 regulators that are useful asmedicament.

More particularly, it relates to

(1) compounds of formula (I)

(wherein all the symbols have the same meanings as defined hereinafter),salts thereof, N-oxides thereof or solvates thereof, or prodrugs of thesame,(2) pharmaceutical compositions comprising compounds of formula (I)

(wherein all the symbols have the same meanings as defined hereinafter),salts thereof, N-oxides thereof or solvates thereof, or prodrugs of thesame,(3) CXCR4 regulator comprising compounds of formula (II)

(wherein all the symbols have the same meanings as defined hereinafter),salts thereof, N-oxides thereof or solvates thereof, or prodrugs of thesame, as an active ingredient, and(4) methods for preparation thereof.

Chemokine is known as a basic protein having endogeneous leukocytechemotactic and activating abilities and strong heparin-bindingabilities. At present, it is considered that chemokine is related to notonly the control of infiltration of specific leukocyte at the time ofinflammations and immune responses but also the development and homingof lymphocyte under physiological conditions and migration of hemocyteprecursor cells and somatic cells.

Differentiation, proliferation and cell death of hemocytes arecontrolled by various types of cytokine In the living body,inflammations are found topically and differentiation, maturation andthe like of lymphocytes are carried out at certain specified sites. Thatis, various necessary cells migrate into certain specified sites andaccumulate therein to cause a series of inflammations and immuneresponses. Accordingly, migration of cells is also an indispensablephenomenon in addition to differentiation, proliferation and death ofcells.

Migration of hemocytes in the living body starts firstly in thedevelopment stage by the shift of hematopoiesis started in the AGMregion into permanent hematopoiesis in bone marrow via fetal liver.Furthermore, precursor cells of T cells and thymus dendritic cellsmigrate from the fetal liver into the bone marrow and then into thethymus gland and cytodifferentiate under thymus environment. The T cellwhich received clone selection migrates into secondary lymphoid tissuesand takes part in an immune response in the periphery. The Langerhans'cell of the skin activated and differentiated by capturing an antigenmigrates into the T cell region of a topical lymph node and activatesnaive T cell therein as a dendritic cell. The memory T cell performs itshoming again into the lymph node via lymphatic and blood vessels. Also,B cell, T cell in the intestinal epithelium, γδ T cell, NKT cell anddendritic cell migrate from bone marrow without passing through thethymus gland and differentiate to take part in an immune response.

Chemokines are deeply involved in these various cell migration. Forexample, an SDF-1 (stromal cell derived factor-1) and its receptor CXCR4act on various immunological and inflammatory reactions. They arereported to be involved in accumulation and activation of CD4+T cells ina synovial membrane derived from a human patient having a rheumatoidarthritis (J. Immunol., 165, 6590-6598 (2000)). In addition, a CXCR4inhibitor suppressed recruitment of leukocytes into a joint also in CIAmodel mice and reduces the arthritis score dramatically (J. Immunol.,167, 4648-4692 (2001)). In a mouse OVA-induced airway hypersensitivitymodel, an anti-CXCR4 antibody reduced the number of eosinophilesrecruited into a pulmonary interstice to suppress the airwayhypersensitivity (J. Immunol., 165, 499-508 (2000)).

SDF-1 and its receptor CXCR4 are also reported to play an important rolein maintaining hemopoietic stem cells in a bone marrow (J. Exp. Med.,185, 111-120 (1997), Blood, 97, 3354-3360 (2001)). Accordingly, theinhibition of SDF-1 and CXCR4 is expected to regulate the recruitment ofthe hemopoietic stem cells into a peripheral blood and to be useful in aperipheral blood stem cell transplantation and this also in aregeneration transplantation therapy.

SDF-1 and CXCR4 are involved in an infiltration of cells of variouscancers such as mammary cancer, prostate cancer and ovarian cancer(Nature, 410, 50-56 (2001), Cancer Res., 62, 1832-1837 (2002), CancerRes., 62, 5930-5938 (2002)), and an anti-CXCR4 antibody inhibitedmetastasis of a mammary cancer cell into a lung in a human mammarycancer cell line transfusion model in SCID mice. Also, since SDF-1 ishighly expressed in a human ovarian epithelial tumor, it promotesaccumulation of a plasmocytic dendric cell to inhibit the action of abone marrow dendric cell involved in a tumor immune, resulting in aninhibition of the tumor immune (Nat. Med., 12, 1339 (2001)). Inaddition, it is involved also in proliferation and movement of anon-hodgkin lymphoma cell, and an anti-CXCR4 antibody inhibitsproliferation of tumor cells in a human non-hodgkin lymphoma celltransfusion model in BID/SCID mice, resulting in an improvement in themortality in mice (Cancer Res., 62, 3106-3112 (2002)).

SDF-1 and CXCR4 play important roles in formation of a hippocampaldentate gyrus granulocyte essential for memory and learning, and areinvolved in progression of an adult disease associated with plasticityand hippocampal pathology such as Alzheimer's disease, cerebral stroke,epilepsy and the like (Development, 129, 4249-4260 (2002), TrendsNeuroscience, 25, 548-549 (2002)).

SDF-1 and CXCR4 are essential for a function of an auto-reactive B cellinvolved in progression of a diabetes, and an anti-SDF-1 antibodyreduced the blood sugar level in NOD mice and reduced the mature IgM+Bcell count in a peripheral tissue (Immunology, 107, 222-232 (2002)).SDF-1 was highly expressed in a human arteriosclerotic plaque, resultingin an activation of platelets (Circ. Res., 86, 131-138 (2000)).

Results observed in SDF-1/CXCR4 knockout mice also indicated that SDF-1is essential for functions of the blood vessels in central nervoustissues, heart and gastrointestinal tracts in addition to lymphocytes(Nature, 382, 635-639 (1996), Nature, 393, 591-594 (1998), Nature, 393,595-599 (1998)). Accordingly, it is believed to be involved in diseasesof such tissues.

Thus, chemokine receptors are greatly related to the control ofinflammation and immune responses through a mechanism in which they areexpressed at certain specified periods in variously specific cells andthe effector cells are accumulated in a region where chemokine isproduced.

Acquired immunodeficiency syndrome (called AIDS) which is induced byhuman immunodeficiency virus (hereinafter referred to as “HIV”) is oneof the diseases of which their therapeutic methods are most earnestlydesired in recent years. Once infection with HIV is completed in aCD4-positive cell which is a principal target cell, HIV repeats itsproliferation in the body of the patient and, sooner or later,completely destroys T cell which takes charge of the immunologicalfunction. During this process, the immunological function is graduallyreduced to cause fever, diarrhea, lymph node enlargement and the likevarious immunodeficiency conditions which are apt to cause complicationswith pneumocystis carinii pneumonia and the like various opportunisticinfections. Such conditions are the onset of AIDS, and it is well knownthat they induce and worsen Kaposi sarcoma and the like malignanttumors.

As the recent preventive and therapeutic methods for AIDS, attempts havebeen made to, e.g., (1) inhibit growth of HIV by the administration of areverse transcriptase inhibitor or a protease inhibitor and (2) preventor alleviate opportunistic infections by the administration of a drughaving immunopotentiation activity.

Helper T cells which take charge of the central of immune system aremainly infected with HIV. It is known since 1985 that HIV uses themembrane protein CD4 expressing on the membrane of T cells in theinfection (Cell, 52, 631 (1985)). The CD4 molecule is composed of 433amino acid residues, and its expression can be found in macrophages,some B cells, vascular endothelial cells, Langerhans' cells in skintissues, dendritic cells in lymphoid tissues, glia cells of the centralnervous system and the like, in addition to the mature helper T cells.However, since it has been revealed that the infection with HIV is notcompleted by the CD4 molecule alone, a possibility has been suggested onthe presence of factors other than the CD4 molecule, which are relatedto the infection of cells with HIV.

In 1996, a cell membrane protein called Fusin was identified as a factorother than the CD4 molecule, which is related to the HIV infection(Science, 272, 872 (1996)). It was confirmed that this Fusin molecule isa receptor (namely, CXCR4) of SDF-1. In addition, it was confirmed alsoin vitro that the SDF-1 specifically inhibits infection of T cell tropic(X4) HIV (Nature, 382, 829 (1996), Nature, 382, 833 (1996)). That is, itis considered that the HIV infection was inhibited by the binding ofSDF-1 to CXCR4 preceding HIV, thereby depriving HIV of a foothold forinfecting cells.

Also at that time, it was discovered that another chemokine receptorCCR5, which is a receptor of RANTES, MIP-1α and MIP-β, is also used atthe time of the infection with a macrophage tropic (R5) HIV (Science,272, 1955 (1996)).

Accordingly, substances which can compete with CXCR4 and CCR5 for HIV,or which can bind to HIV virus thus causing the virus unable to bind toCXCR4 and CCR5, could become HIV infection inhibitors. Also, there is acase in which a low molecular compound initially discovered as an HIVinfection inhibitor was actually a CXCR4 antagonist (Nature Medicine, 4,72 (1998)).

Based on the above, a chemokine and a chemokine receptor are deeplyinvolved in inflammation, immune disease or HIV infection. A compoundhaving an ability of regulating CXCR4 is effective in treatment andprevention, for example, of an inflammatory/immune disease, allergicdisease, infectious disease, especially HIV infection and accompanyingdiseases, psychoneurotic disease, cerebral disease, cardiovasculardisease, metabolic disease and cancerous disease. In addition, it isalso useful in cell medicine and regeneration medicine. The cellmedicine includes peripheral blood stem cell recruitment and in vitroand in vivo proliferation of a stem cell for the purpose of a genetherapy. The regeneration medicine includes transplantation medicinesuch as various organ transplantations including bone marrowtransplantation, peripheral blood stem cell transplantation and tissuerepair. The transplantation medicine agent is an agent used in the bonemarrow transplantation, peripheral blood stem cell transplantation orvarious organ transplantation. The transplantation medicine agentincludes, for example, an infection-preventing agent orimmunosuppressant. Those included also are agents intended to supplementand/or enhance the therapeutic effect in the regeneration medicine. Antransplantation medicine agent has an effect, for example, of migratinga stem cell from a bone marrow into a peripheral blood or to increaseleukocyte rapidly to a normal level.

The inflammatory/immune diseases include, for example, rheumatoidarthritis, arthritis, gout, transplanted organ rejection, graft versushost disease (GVHD), nephritis, psoriasis, rhinitis, conjunctivitis,multiple sclerosis, ulcerative colitis, Crohn's disease, shockaccompanied with bacterial infection, pulmonary fibrosis, systemicresponse syndrome (SIRS), acute pulmonary disorder, diabetes and thelike.

The allergic diseases include, for example, asthma, atopic dermatitis,rhinitis, conjunctivitis and the like.

The infectious diseases, especially HIV infection and accompanyingdiseases, include, for example, acquired immunodeficiency syndrome(AIDS), candidosis, carinii pneumonia, cytomegalovirus retinitis,Kaposi's sarcoma, malignant lymphoma, AIDS encephalopathy, bacterialsepsis and the like.

The psychoneurotic diseases and the cerebral diseases include, forexample, dementia such as Alzheimer's disease, Parkinson's disease,cerebral stroke, cerebral infarction, cerebral hemorrhage, epilepsy,schizophrenia, peripheral nervous disorder and the like.

The cardiovascular diseases include, for example, arteriosclorosis,ischemic reperfusion injury, hypertension, myocardial infarction, anginapectoris, cardiac insufficiency and the like.

The metabolic diseases include, for example, diabetes, osteoporosis,prostatic hypertrophy, pollakiuia and the like.

The cancerous diseases include, for example, mammary cancer, malignanttumor such as malignant lymphoma, cancer metastasis,post-radiotherapy/chemotherapy bone marrow suppression orthrombocytopenia and the like.

BACKGROUND ART

In specification of WO01/14333, it is described that piperazine orpiperidine derivates of formula (A)

are chemokine receptor (specifically CCR1 or CCR3) regulator, and theyare useful as treatment for inflammatory diseases, autoimmune diseases,gastrointestinal discomforts, HIV diseases and systemic diseases etc.

In specification of WO00/58305, it is described that 1,4-piperidinederivatives of formula (B)

are useful for diseases related to chemokine receptor.

In specification of JP-A-6-192235, it is described that quinazolinederivatives of formula (C)

having an effect of inhibiting cGMP phosphodiesterase and TXA2.

In specification of U.S. Pat. No. 3,956,495, it is described thatN-[4-(4-morpholinyl)-2-quinazolinyl]-1,2-ethanediamine dihydrochloride(CAS No. 59870-53-0),N,N-diethyl-N′-[2-(1-pyrrolidinyl)-4-quinazolinyl]-1,2-ethanediamine(CAS No. 59870-50-70) andN,N-diethyl-N′-[2-(1-pyrrolidinyl)-4-quinazolinyl]-1,2-ethanediaminedihydrochloride (CAS No. 59870-51-8) are having an effect of inhibitingplatelet aggregation.

In specification of JP-A-3-14568,N,N-diethyl-N′-[2-(4-phenyl-1-piperidinyl)-4-pyrimidinyl]-1,2-ethylenediamine(CAS No. 131039-38-8) is described as nervous system drugs.

In specification of WO95/05383,N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N′-[2-(1-piperidinyl)-4-pyrimidinyl]-1,3-propanediamineoxalate (CAS No. 169747-23-3) is having an effect of vasoconstriction.

In specification of DE1794396, it is described that7-[4-[4,6-bis(hexahydro-1H-azepin-1-yl)-1,3,5-triazin-2-yl]amino-2H-1,2,3-triazol-2-yl]-3-phenyl-2H-1-benzopyran-2-one(CAS No. 19695-38-6) is useful as fluorescent brightening agent.

In specification of JP-A-51-9759,N-[4-(hexahydro-1H-azepin-1-yl)thieno[3,2-d]pyrimidin-2-yl-1,4-butanediamine(CAS No. 31895-98-4) is described.

Other than those above,N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N′-[2-(1-piperidinyl)-4-pyrimidinyl]-1,3-propanediamine(CAS No. 169747-22-2),4-ethoxy-6-(hexahydro-1H-azepin-1-yl)-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine(CAS No. 295344-71-7),4-(hexahydro-1H-azepin-1-yl)-6-methyl-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine(CAS No. 332167-02-9),4-chloro-6-(hexahydro-1H)-azepin-1-yl)-N-[2-(4-morpholinyl)ethyl]-1,3,5-triazin-2-amine(CAS No. 337484-66-9),4-(hexahydro-1H-azepin-1-yl)-6-methoxy-N-[3-(4-morpholinyl)propyl-1,3,5-triazin-2-amine(CAS No. 384845-62-9) are known.

DISCLOSURE OF THE INVENTION

It is desired that safety CXCR4 regulators that are useful aspreventives and/or treatments for various inflammatory diseases, variousallergic diseases, acquired immunodeficiency syndrome, infection withhuman immunodeficiency virus, or agents for regeneration therapy aredeveloped.

In order to find a compound binding CXCR4, the present inventors haveconducted intensive studies and found that the compounds represented byformulae (I) and (II), salts thereof, N-oxides thereof or solvatesthereof, or prodrugs of the same regulate CXCR4 and they are useful aspreventing and/or treatment for various diseases, and thus the presentinvention has been accomplished.

The present invention relates to

[1] a compound represented by formula (I):

wherein ring A represents a nitrogen-containing heterocyclic group whichmay have a substituent(s); ring B represents a homocyclic group whichmay have a substituent(s) or a heterocyclic group which may have asubstituent(s); and Y represents a hydrocarbon group which may have asubstituent(s), a heterocyclic group which may have a substituent(s), anamino group which may be protected, a hydroxyl group which may beprotected or a mercapto group which may be protected,

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof,

[2] the compound according to the above-described [1], wherein ring A isa 5- to 10-membered nitrogen-containing heterocyclic group which mayhave a substituent(s),[3] the compound according to the above-described [1], wherein ring B isa nitrogen-containing heterocyclic group which may have asubstituent(s),[4] the compound according to the above-described [1], wherein Y is

wherein G represents a bond or a spacer containing 1 to 3 atoms as amain chain; ring J represents a 4- to 7-membered nitrogen-containingheterocyclic group; and W represents hydrogen, a hydrocarbon group whichmay have a substituent(s) or a heterocyclic group which may have asubstituent(s),

[5] the compound according to the above-described [1], which isrepresented by formula (I-1):

wherein ring A¹ represents a 5- to 10-membered nitrogen-containingsaturated heterocyclic group which may have a substituent(s), or a 5- to10-membered nitrogen-containing heterocyclic group which has one doublebond and which may have a substituent(s); ring B¹ represents a 6- to11-membered nitrogen-containing monocyclic or bicyclic heterocyclicgroup which may have a substituent(s); and other symbols have the samemeanings as those described in the above-described [4],

[6] the compound according to the above-described [1], which isrepresented by formula (I-2):

wherein all symbols have the same meanings as those described in theabove-described [1] or [4],

[7] a compound represented by formula (I-A):

wherein ring A^(A) represents a 4- to 15-membered monocyclic, bicyclicor tricyclic heterocyclic group which is saturated or has one doublebond and which contains at least one nitrogen atom and may furthercontain 1 to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfuratom;

ring B^(A) represents B^(A1) or B^(A2);

B^(A1) represents:

B^(A2) represents:

R⁴ represents (i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenyl or C2-15alkynyl which may be substituted with 1 to 5 of R¹⁰, (iii) a C3-8carbocyclic group which may be substituted with 1 to 5 of R³, (iv) a 5-to 15-membered heterocyclic group which contains 1 or 2 nitrogen atoms,1 or 2 oxygen atoms and/or one sulfur atom and which may be substitutedwith 1 to 5 of R³, (v) COR⁵ wherein R⁵ represents C1-15 alkyl, C2-15alkenyl, C2-15 alkynyl or phenyl, or (vi) COOR⁶ wherein R⁶ representsC1-15 alkyl, C2-15 alkenyl, C2-15 alkynyl or phenyl; the upward arrowrepresents a binding position to ring A^(A); and the right-downwardarrow represents a binding position to the nitrogen atom bound to L;

L represents (1) a bond, (2) C1-8 alkylene, C2-8 alkenylene or C2-8alkynylene, wherein the alkylene, alkenylene and alkynylene each may besubstituted with 1 to 5 of R¹⁰, or (3) a C3-8 carbocyclic group whichmay be substituted with R³;

Q represents (1) NR¹R² wherein R¹ and R² each independently represents(i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenyl or C2-15 alkynyl which maybe substituted with 1 to 5 of R¹⁰, (iii) a C3-8 carbocyclic group whichmay be substituted with 1 to 5 of R³, or (iv) a 5- to 15-memberedheterocyclic group which contains 1 or 2 nitrogen atoms, 1 or 2 oxygenatoms and/or one sulfur atom and which may be substituted 1 to 5 of R³,or (2) ring C;

ring C represents a 4- to 15-membered heterocyclic group which containsat least one nitrogen atom and may further contain 1 or 2 nitrogenatoms, 1 or 2 oxygen atoms and/or one sulfur atom and which may besubstituted with 1 to 5 of R³;

plural R³'s each independently represents (1) C1-15 alkyl, C2-15 alkenylor C2-15 alkynyl, wherein the alkyl, alkenyl and alkynyl may besubstituted with 1 to 5 of R¹⁰, (2) oxo, or (3)R¹⁰;

plural R¹⁰'s each independently represents (1) OR¹¹, (2) OCOR¹², (3)OCOOR¹³, (4) NR¹⁴R¹⁵, (5) NR¹⁶COR¹², (6) NR¹⁶CONR¹⁴R¹⁵, (7) NR¹⁶COOR¹³,(8) COOR¹³, (9) COR¹², (10) CONR¹⁴R¹⁵, (11) SO₂R¹², (12) SOR²², (13)SO₂NR²⁴R²⁵, (14) NR¹⁶SO₂R¹², (15) B(OH)₂, (16) SR¹¹, (17) halogen, (18)nitro, (19) cyano, or (20) ring D;

R¹¹ represents (i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenyl or C2-15alkynyl, wherein the alkyl, alkenyl and alkynyl may be substituted with1 to 5 of halogen, NR¹⁴R¹⁵, OR²¹, SR²¹, COOR¹³, or ring D, or (iii) ringD;

R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independently represents (i) hydrogen,(ii) C1-15 alkyl, C2-15 alkenyl or C2-15 alkynyl which may besubstituted with ring D, or (iii) ring D;

ring D represents a C3-15 monocyclic, bicyclic or tricyclic carbocyclicgroup, or a 5- to 15-membered monocyclic, bicyclic or tricyclicheterocyclic group which contains 1 to 4 nitrogen atoms, 1 or 2 oxygenatoms and/or one sulfur atom; and

ring D may be substituted with 1 to 5 of the groups selected from thefollowing (1) to (22):

(1) C1-15 alkyl, C2-15 alkenyl or C2-15 alkynyl, wherein the alkyl,alkenyl or alkynyl may be substituted with 1 to 5 of OR²¹, OCOR²²,OCOOR²³, NR²⁴R²⁵, NR²⁶COR²², NR²⁶CONR²⁴R²⁵, NR²⁶COOR²³, COOR²³, COR²²,CONR²⁴R²⁵, SO₂R²², SOR²², SO₂NR²⁴R²⁵, NR²⁶SO₂R²², B(OH)₂, SR²¹, halogen,nitro or cyano, (2) oxo, (3) OR²¹, (4) OCOR²², (5) OCOOR²³, (6) NR²⁴R²⁵,(7) NR²⁶COR²², (8) NR²⁶CONR²⁴R²⁵, (9) NR²⁶COOR²³, (10) COOR²³, (11)COR²², (12) CONR²⁴R²⁵, (13) SO₂R²², (14) SOR²², (15) SO₂NR²⁴R²⁵, (16)NR²⁶SO₂R²², (17) B(OH)₂, (18) SR²¹, (19) halogen, (20) nitro, (21) cyanoor (22) ring E;

R²¹ represents (i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenyl or C2-15alkynyl which may be substituted with COR²², NR²⁴R²⁵ or ring E, or (iii)ring E;

R²², R²³, R²⁴, R²⁵ and R²⁶ each independently represents (i) hydrogen,(ii) C1-15 alkyl, C2-15 alkenyl or C2-15 alkynyl which may besubstituted with ring E, or (iii) ring E;

ring E represents a C3-15 monocyclic, bicyclic or tricyclic carbocyclicgroup, or a 5- to 15-membered monocyclic, bicyclic or tricyclicheterocyclic group which contains 1 to 4 nitrogen atoms, 1 or 2 oxygenatoms and/or one sulfur atom, and

ring E may be substituted with 1 to 5 of (i) C1-15 alkyl which may besubstituted with phenyl, (ii) halogen, (iii) phenyl, (iv) C1-15 alkoxy,(v) hydroxyl, (vi) amino, (vii) mono(C1-8 alkyl)amino, or (viii) di(C1-8alkyl)amino;

ring A^(A) may be substituted with 1-5 of R^(a);

ring B^(A) may be substituted with 1-5 of R^(b));

R^(a) and R^(b)) each independently represents a group which has thesame meaning as the group represented by R³; and

wherein the following compounds (1) to (6) are excluded:

-   (1) N-[4-(4-morpholinyl)-2-quinazolinyl]-1,2-ethanediamine    dihydrochloride,-   (2)    N,N-dimethyl-N′-[2-(4-phenyl-1-piperidinyl)-4-pyrimidinyl]-1,2-ethylenediamine,-   (3)    N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N′-[2-(1-piperidinyl)-4-pyrimidinyl]-1,3-propanediamine,-   (4)    N-[(3,4-dihydro-2H-1-benzopyrane-2-yl)methyl]-N′-[2-(1-piperidinyl)-4-pyrimidinyl]-1,3-propanediamine    oxalate,-   (5)    N,N-diethyl-N′-[2-(1-pyrrolidinyl)-4-quinazolinyl-1,2-ethanediamine,    and-   (6)    N,N-diethyl-N′-[2-(1-pyrrolidinyl)-4-quinazolinyl-1,2-ethanediamine    dihydrochloride,

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof,

[8] a compound represented by formula (I-B):

wherein ring A^(B) represents a 7- to 15-membered monocyclic, bicyclicor tricyclic heterocyclic group which is saturated or contains onedouble bond and which contains at least one nitrogen atom and mayfurther contain 1 to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or onesulfur atom;

ring B^(B) represents:

wherein ring Z represents a C5-10 monocyclic or bicyclic carbocyclicgroup, or a 5- to 10-membered monocyclic or bicyclic heterocyclic groupwhich may contain 1 or 2 nitrogen atoms, one oxygen atom and/or onesulfur atom; the upward arrow represents a binding position to ringA^(B); and the right-downward arrow represents a binding position to thenitrogen atom bound to L;

ring A^(B) may be substituted with 1 to 5 of R^(a); ring B^(B) may besubstituted with 1 to 5 of R^(b); and R^(a), R^(b) and other symbolshave the same meanings as those described in the above-described [7],and

wherein the following compounds (1) to (7) are excluded:

-   (1)    N-[4-(hexahydro-1H-azepin-1-yl)thieno[3,2-d]pyrimidin-2-yl]-1,4-butandiamine    dihydrochloride,-   (2)    7-[4-[4,6-bis(hexahydro-1H-azepin-1-yl)-1,3,5-triazin-2-yl]amino-2H-1,2,3-triazol-2-yl]-3-phenyl-2H-1-benzopyran-2-one,-   (3)    4-ethoxy-6-(hexahydro-1H-azepin-1-yl)-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine,-   (4)    4-(hexahydro-1H-azepin-1-yl)-6-methyl-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine,-   (5)    4-chloro-6-(hexahydro-1H)-azepin-1-yl)-N-[2-(4-morpholinyl)ethyl]-1,3,5-triazin-2-amine,-   (6)    4-(hexahydro-1H-azepin-1-yl)-6-methoxy-N-[3-(4-morpholinyl)propyl-1,3,5-triazin-2-amine,    and-   (7)    N-[4-(hexahydro-1H-azepin-1-yl)thieno[3,2-d]pyrimidin-2-yl-1,4-butanediamine,    or

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof,

[9] the compound according to any one of the above-described [1], [7]and [8], which is

-   (1) N-(4-azepan-1-ylpyrimidin-2-yl)ethane-1,2-diamine,-   (2)    N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine,-   (3)    4-azepan-1-yl-N-((3S)-1-cyclohexylpyrrolidin-3-yl)pyrimidin-2-amine,-   (4) 4-azepan-1-yl-N-((3S)-1-benzylpyrrolidin-3-yl)pyrimidin-2-amine,-   (5)    4-azepan-1-yl-N-((3S)-1-(2-ethylbutyl)piperidin-3-yl)pyrimidin-2-amine,-   (6)    4-azepan-1-yl-N-[(3S)-1-cyclohexylpiperidin-3-yl]pyrimidin-2-amine,-   (7)    4-azepan-1-yl-N-[(3S)-1-tetrahydro-2H-pyran-4-ylpiperidin-3-yl]pyrimidin-2-amine,-   (8)    4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yk)amino]piperidin-1-ylcyclohexanol,    or-   (9)    (3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclohexylcarbonyl)-1,4′-bipiperidin-3-amine,    [10] a pharmaceutical composition, which comprises a compound    represented by formula (I):

wherein all symbols have the same meanings as those described in theabove-described [1],

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof,

[11] the pharmaceutical composition according to the above-described[10], which is a CXCR4 regulating agent,[12] the pharmaceutical composition according to the above-described[11], wherein the CXCR4 regulating agent is a CXCR4 antagonist,[13] the pharmaceutical composition according to the above-described[12], which is a preventive and/or therapeutic agent for humanimmunodeficiency virus infection,[14] the pharmaceutical composition according to the above-described[13], which is a preventive and/or therapeutic agent for acquiredimmunodeficiency syndrome,[15] the pharmaceutical composition according to the above-described[10], which is an agent for regeneration medicine,[16] the pharmaceutical composition according to the above-described[15], wherein the agent for regeneration medicine is an agent fortransplantation medicine,[17] a CXCR4 regulating agent, which comprises a compound represented byformula (II):

wherein T represents

wherein R¹⁰¹ and R¹⁰² each independently represents hydrogen or ahydrocarbon group which may have a substituent(s); ring A has the samemeaning as that described in the above-described [1]; and other symbolshave the same meanings as those described in the above-described [1],

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof, as an active ingredient,

[18] the agent according to the above-described [17], wherein the CXCR4regulating agent is a CXCR4 antagonist,[19] a CXCR4 regulating agent, which comprises a compound represented byformula (I-3):

wherein ring A² represents a 4- to 15-membered monocyclic, bicyclic ortricyclic heterocyclic group which contains at least one nitrogen atomand may further contain 1 to 3 nitrogen atoms, 1 or 2 oxygen atomsand/or one sulfur atom; ring B² represents a 5- to 15-memberedmonocyclic, bicyclic or tricyclic heterocyclic group which contains atleast one nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1or 2 oxygen atoms and/or one sulfur atom; ring A² may be substitutedwith 1 to 5 of R^(a); ring B² may be substituted with 1 to 5 of R^(b);and R^(a), R^(b) and other symbols have the same meanings as thosedescribed in the above-described [7],

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof, as an active ingredient,

[20] the CXCR4 regulating agent according to the above-described [19],which is a CXCR4 antagonist,

[21] a CXCR4 regulating agent, which comprises the compound representedby formula (I-A) according to the above-described [7], a salt thereof,an N-oxide thereof, a solvate thereof, or a prodrug thereof, as anactive ingredient,

[22] the CXCR4 regulating agent according to the above-described [21],which is a CXCR4 antagonist,[23] a CXCR4 regulating agent, which comprises the compound representedby formula (I-B) according to the above-described [8], a salt thereof,an N-oxide thereof, a solvate thereof, or a prodrug thereof, as anactive ingredient,[24] the CXCR4 regulating agent according to the above-described [23],which is a CXCR4 antagonist,[25] the CXCR4 regulating agent according to the above-described [17] or[19], which is a preventive and/or therapeutic agent forinflammatory/immune diseases, allergic diseases, infectious diseases,HIV infection or diseases accompanied therewith, psychoneuroticdiseases, cerebral diseases, cardiovascular diseases, metabolic diseasesand cancerous diseases,[26] the CXCR4 regulating agent according to the above-described [25],which is a preventive and/or therapeutic agent for HIV infection ordiseases accompanied therewith,[27] the CXCR4 regulating agent according to the above-described [17] or[19], which is useful for regeneration medicine,[28] a medicament which comprises the compound according to any one ofthe above-described [1], [7], [8] and [17], a salt thereof, an N-oxidethereof, a solvate thereof, or a prodrug thereof, in combination withone or at least two of a reverse transferase inhibitor, a proteaseinhibitor, a CCR2 antagonist, a CCR3 antagonist, a CCR4 antagonist, aCCR5 antagonist, a fusion inhibitor, an antibody against a surfaceantigen of HIV-1, and a vaccine of HIV-1,[29] the medicament according to the above-described [28], wherein thereverse transferase inhibitor is one or at least two selected fromzidovudine, didanosine, zalcitabine, stavudine, lamivudine, abacavir,adefovir, dipivoxil, emtricitabine, tenofovir, nevirapine, nevirapine,efavirenz and capravirine,[30] the medicament according to the above-described [28], wherein theprotease inhibitor is one or at least two selected from indinavir,ritonavir, nelfinavir, saquinavir, amprenavir, lopinavir and lopinavir,[31] a method for antagonizing CXCR4 in a mammal, which comprisesadministering to a mammal an effective amount of a compound representedby formula (II):

wherein all symbols have the same meanings as those described in theabove-described [1] or [17],

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof,

[32] use of a compound represented by formula (II):

wherein all symbols have the same meanings as described in theabove-described [1] or [17],

a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof for the manufacture of a CXCR4 antagonist.

DETAILED DESCRIPTION

The “nitrogen-containing heterocycle” in the “nitrogen-containingheterocyclic group which may have a substituent(s)” represented by ringA in the compound represented by formula (I) according to the presentinvention refers to a monocyclic, bicyclic or tricyclic heterocyclewhich may contain, in addition to the nitrogen atom indicated in ring Ain formula (I), 1 to 6 hetero atoms selected from nitrogen, oxygen andsulfur atoms. The “nitrogen-containing heterocycle” includes, forexample, a “3- to 15-membered nitrogen-containing unsaturatedmonocyclic, bicyclic or tricyclic heterocycle”, “3- to 15-memberednitrogen-containing saturated monocyclic, bicyclic or tricyclicheterocycle” and the like.

The “3- to 15-membered nitrogen-containing unsaturated monocyclic,bicyclic or tricyclic heterocycle” includes, for example, pyrrole,imidazole, triazole, tetrazole, pyrazole, azepine, diazepine, indole,isoindole, indazole, purine, benzimidazole, benzazepine, benzodiazepine,benzotriazole, carbazole, beta-carboline, phenothiazine, phenoxazine,perimidine, pyrroline, imidazoline, triazoline, tetrazoline, pyrazoline,dihydropyridine, tetrahydropyridine, dihydropyrazine,tetrahydropyrazine, dihydropyrimidine, tetrahydropyrimidine,dihydropyridazine, tetrahydropyridazine, dihydroazepine,tetrahydroazepine, dihydrodiazepine, tetrahydrodiazepine,dihydrooxazole, dihydroisoxazole, dihydrothiazole, dihydroisothiazole,dihydrofurazan, dihydrooxadiazole, dihydrooxazine, dihydrooxadiazine,dihydrooxazepine, tetrahydrooxazepine, dihydrooxadiazepine,tetrahydrooxadiazepine, dihydrothiadiazole, dihydrothiazine,dihydrothiadiazine, dihydrothiazepine, dihydrothiadiazepine,tetrahydrothiadiazepine, indoline, isoindoline, dihydroindazole,dihydroquinoline, tetrahydroquinoline, dihydroisoquinoline,tetrahydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine,dihydronaphthyridine, tetrahydronaphthyridine, dihydroquinoxaline,tetrahydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline,dihydrocinnoline, tetrahydrocinnoline, dihydrobenzoxazine,dihydrobenzothiazine, pyrazinomorpholine, dihydrobenzoxazole,dihydrobenzothiazole, dihydrobenzimidazole, dihydrobenzazepine,tetrahydrobenzazepine, dihydrobenzodiazepine, tetrahydrobenzodiazepine,dihydrobenzoxazepine, tetrahydrobenzoxazepine, dihydrocarbazole,tetrahydrocarbazole, dihydroacridine, tetrahydroacridine,hexahydroazocine, hexahydroazonine, hexahydrodiazocine,hexahydrodiazonine, octahydroazecine, octahydrodiazecine ring etc.

The “3- to 15-membered nitrogen-containing saturated monocyclic,bicyclic or tricyclic heterocycle” includes, for example, aziridine,azetidine, pyrrolidine, imidazolidine, triazolidine, tetrazolidine,pyrazolidine, piperidine, piperazine, perhydropyrimidine,perhydropyridazine, perhydroazecine, perhydrodiazepine, perhydroazocine,tetrahydrooxazole (oxazolidine), tetrahydroisoxazole (isoxazolidine),tetrahydrothiazole (thiazolidine), tetrahydroisothiazole(isothiazolidine), tetrahydrofurazan, tetrahydrooxadiazole(oxadiazolidine), tetrahydrooxazine, tetrahydrooxadiazine,perhydrooxazepine, perhydrooxadiazepine, tetrahydrothiadiazole(thiadiazolidine), tetrahydrothiazine, tetrahydrothiadiazine,tetrahydrothiazepine, perhydrothiazepine, perhydrothiadiazepine,morpholine, thiomorpholine, perhydroindazole, perhydroquinoline,perhydroisoquinoline, perhydrophthalazine, perhydronaphthyridine,perhydroquinoxaline, perhydroquinazoline, perhydrocinnoline,perhydrobenzoxazole, perhydrobenzothiazole, perhydrobenzimidazole,perhydrocarbazole, perhydroacridine, perhydroazonine, perhydroazecine,azaundecane, azadodecane, azamidecane, azatetradecane, azapentadecane,perhydrodiazocine, perhydrodiazonine, perhydrodiazecine, diazaundecane,diazadodecane, diazatridecane, diazatetradecane, diazapentadecane,perhydroindole, perhydroisoindole, perhydro-beta-carboline,perhydrophenazine, perhydrophenothiadine, perhydrophenoxadine,perhydrophenanthridine, perhydrophenanthroline, perhydroperimidine,azabicyclo[3.2.2]nonane, azabicyclo[3.3.2]decane,azabicyclo[2.2.2]octane, azabicyclo[3.3.3]undecane,azabicyclo[4.3.3]dodecane, azabicyclo[4.4.3]tridecane,azabicyclo[4.4.4]tetradecane etc.

The “Nitrogen-containing heterocycle” represented by ring A ispreferably “5- to 10-membered nitrogen-containing heterocycle”.Concretely, “5- to 10-membered nitrogen-containing unsaturatedheterocycle” includes, for example, pyrrole, imidazole, triazole,tetrazole, pyrazole, azepine, diazepine, indole, isoindole, indazole,purine, benzimidazole, benzotriazole, pyrroline, imidazoline,triazoline, tetrazoline, pyrazoline, dihydropyridine,tetrahydropyridine, dihydropyrazine, tetrahydropyrazine,dihydropyrimidine, tetrahydropyrimidine, dihydropyridazine,tetrahydropyridazine, dihydroazepine, tetrahydroazepine,dihydrodiazepine, tetrahydrodiazepine, dihydrooxazole, dihydroisoxazole,dihydrothiazole, dihydroisothiazole, dihydrofurazan, dihydrooxadiazole,dihydrooxazine, dihydrooxadiazine, dihydrooxazepine,tetrahydrooxazepine, dihydrooxadiazepine, tetrahydrooxadiazepine,dihydrothiadiazole, dihydrothiazine, dihydrothiadiazine,dihydrothiazepine, tetrahydrothiazepine, dihydrothiadiazepine,tetrahydrothiadiazepine, indoline, isoindoline, dihydroindazole,dihydroquinoline, tetrahydroquinoline, dihydroisoquinoline,tetrahydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine,dihydronaphthyridine, tetrahydronaphthyridine, dihydroquinoxaline,tetrahydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline,dihydrocinnoline, tetrahydrocinnoline, dihydrobenzoxazine,dihydrobenzothiazine, pyrazinomorpholine, dihydrobenzoxazole,dihydrobenzothiazole, dihydrobenzimidazole, hexahydroazocine,hexahydroazonine, hexahydrodiazocine, hexahydrodiazonine,octahydroazecine, octahydrodiazecine ring etc.

The “5- to 10-membered nitrogen-containing saturated heterocycle”includes, for example, pyrrolidine, imidazolidine, triazolidine,tetrazolidine, pyrazolidine, piperidine, piperazine, perhydropyrimidine,perhydropyridazine, perhydroazepine, perhydrodiazepine, perhydroazocine,tetrahydrooxazole (oxazolidine), tetrahydroisoxazole (isoxazolidine),tetrahydrothiazole (thiazolidine), tetrahydroisothiazole(isothiazolidine), tetrahydrofurazan, tetrahydrooxadiazole(oxadiazolidine), tetrahydrooxazine, tetrahydrooxadiazine,perhydrooxazepine, perhydrooxadiazepine, tetrahydrothiadiazole(thiadiazolidine), tetrahydrothiazine, tetrahydrothiadiazine,perhydrothiazepine, perhydrothiadiazepine, morpholine, thiomorpholine,perhydroindazole, perhydroquinoline, perhydroisoquinoline,perhydrophthalazine, perhydronaphthyridine, perhydroquinoxaline,perhydroquinazoline, perhydrocinnoline, perhydrobenzoxazole,perhydrobenzothiazole, perhydrobenzimidazole, perhydroazonine,perhydroazecine, perhydrodiazocine, perhydrodiazonine,perhydrodiazecine, perhydroindole, perhydroisoindole,azabicyclo[3.2.2]nonane, azabicyclo[3.3.2]decane,azabicyclo[2.2.2]octane etc.

More preferably, ring A is perhydroazepine, perhydroazocine, piperidine,

Ring A may be substituted with 1 to 5 of R^(a) (R^(a) has the samemeaning as R³ which has the same meanings as described above.)

The “Homocycle” in the “homocyclic group which may have asubstituent(s)” represented by ring B includes, for example, a “cyclichydrocarbon” etc. The “cyclic hydrocarbon” includes, for example,“unsaturated cyclic hydrocarbon” or “saturated cyclic hydrocarbon”. The“saturated cyclic hydrocarbon” includes, for example, “3- to 15-memberedsaturated cyclic hydrocarbon” such as cycloalkane which includescyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane,cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane,cyclotridecane, cyclotetradecane or cyclopentadecane etc;perhydropentalene; perhydroazulene; perhydroindene; perhydronaphthalene;perhydroheptalene; spiro[4.4]nonane; spiro[4.5]decane;spiro[5.5]undecane; bicyclo[2.2.1]heptane; bicyclo[3.1.1]heptane;bicyclo[2.2.2]octane; adamantane; noradamantane etc. The “unsaturatedcyclic hydrocarbon” includes, for example, “3- to 15-memberedunsaturated cyclic hydrocarbon” such as cycloalkene which iscyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclopentadiene,cyclohexadiene, cycloheptadiene or cyclooctadiene etc; benzene;pentalene; azulene; indene; indan; naphthalene; dihydronaphthalene;tetrahydronaphthalene; heptalene; biphenylene; as-indacene; s-indacene;acenaphthene; acenaphthylene; fluorene; phenalene; phenanthrene;anthracene; bicyclo[2.2.1]hept-2-ene; bicyclo[3.1.1]hept-2-ene;bicyclo[2.2.2]oct-2-ene etc.

The “heterocycle” in The “heterocyclic group which may have asubstituent(s)” represented by ring B refers to a monocyclic, bicyclicor tricyclic heterocycle which may contain 1 to 7 hetero atoms selectedfrom nitrogen, oxygen and sulfur atoms. The “heterocycle” includes, forexample, a “3- to 15-membered unsaturated monocyclic, bicyclic ortricyclic heterocycle”, a “3- to 15-membered saturated monocyclic,bicyclic or tricyclic heterocycle” and the like.

The “3- to 15-membered unsaturated monocyclic, bicyclic or tricyclicheterocycle” includes, for example, pyrrole, imidazole, triazole,tetrazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine,triazine, azepine, diazepine, furan, pyran, oxepine, thiophene,thiopyran, thiepine, oxazole, isoxazole, thiazole, isothiazole, furazan,oxadiazole, oxazine, oxadiazine, oxazepine, oxadiazepine, thiadiazole,thiazine, thiadiazine, thiazepine, thiadiazepine, indole, isoindole,indolizine, benzofuran, isobenzofuran, benzothiophene,isobenzothiophene, dithianaphthalene, indazole, quinoline, isoquinoline,quinolizine, purine, phthalazine, pteridine, naphthyridine, quinoxaline,quinazoline, cinnoline, benzoxazole, benzothiazole, benzimidazole,chromene, benzoxepine, benzoxazepine, benzoxadiazepine, benzothiepine,benzothiazepine, benzothiadiazepine, benzazepine, benzodiazepine,benzofurazan, benzothiadiazole, benzotriazole, carbazole,beta-carboline, acridine, phenazine, dibenzofuran, xanthene,dibenzothiophene, phenothiazine, phenoxazine, phenoxathiin, thianthrene,phenanthridine, phenanthroline, perimidine, pyrroline, imidazoline,triazoline, tetrazoline, pyrazoline, dihydropyridine,tetrahydropyridine, dihydropyrazine, tetrahydropyrazine,dihydropyrimidine, tetrahydropyrimidine, dihydropyridazine,tetrahydropyridazine, tetrahydrotriazine, dihydroazepine,tetrahydroazepine, dihydrodiazepine, tetrahydrodiazepine, dihydrofuran,dihydropyran, dihydrooxepine, tetrahydrooxepine, dihydrothiophene,dihydrothiopyran, dihydrothiepine, tetrahydrothiepine, dihydrooxazole,dihydroisoxazole, dihydrothiazole, dihydroisothiazole, dihydro furazan,dihydrooxadiazole, dihydrooxazine, dihydrooxadiazine, dihydrooxazepine,tetrahydrooxazepine, dihydrooxadiazepine, tetrahydrooxadiazepine,dihydrothiadiazole, dihydrothiazine, dihydrothiadiazine,dihydrothiazepine, tetrahydrothiazepine, dihydrothiadiazepine,tetrahydrothiadiazepine, indoline, isoindoline, dihydrobenzofuran,dihydroisobenzofuran, dihydrobenzothiophene, dihydroisobenzothiophene,dihydroindazole, dihydroquinoline, tetrahydroquinoline,dihydroisoquinoline, tetrahydroisoquinoline, dihydrophthalazine,tetrahydrophthalazine, dihydronaphthyridine, tetrahydronaphthyridine,dihydroquinoxaline, tetrahydroquinoxaline, dihydroquinazoline,tetrahydroquinazoline, dihydrocinnoline, tetrahydrocinnoline,benzoxathiane, dihydrobenzoxazine, dihydrobenzothiazine,pyrazinomorpholine, dihydrobenzoxazole, dihydrobenzothiazole,dihydrobenzimidazole, dihydrobenzazepine, tetrahydrobenzazepine,dihydrobenzodiazepine, tetrahydrobenzodiazepine, benzodioxepane,dihydrobenzoxazepine, tetrahydrobenzoxazepine, dihydrocarbazole,tetrahydrocarbazole, dihydro-beta-carboline, tetrahydro-beta-carboline,dihydroacridine, tetrahydroacridine, dihydrodibenzofuran,dihydrodibenzothiophene, tetrahydrodibenzofuran,tetrahydrodibenzothiophene, dioxaindan, benzodioxane, chroman,benzodithiolane, benzodithiane,6,7,8,9-tetrahydro-5H-pyrido[4′,3′:4,5]pyrrolo[2,3-b]pyridine,2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole,6,7,8,9-tetrahydro-5H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine,

“3- to 15-membered saturated monocyclic, bicyclic or tricyclicheterocycle” includes, for example, aziridine, azetidine, pyrrolidine,imidazolidine, triazolidine, tetrazolidine, pyrazolidine, piperidine,piperazine, perhydropyrimidine, perhydropyridazine, perhydroazepine,perhydrodiazepine, perhydroazocine, oxirane, oxetane, tetrahydrofuran,tetrahydropyran, perhydrooxepine, thiirane, thietane,tetrahydrothiophene, tetrahydrothiopyran, perhydrothiepine,tetrahydrooxazole (oxazolidine), tetrahydroisoxazole (isoxazolidine),tetrahydrothiazole (thiazolidine), tetrahydroisothiazole(isothiazolidine), tetrahydrofurazan, tetrahydrooxadiazole(oxadiazolidine), tetrahydrooxazine, tetrahydrooxadiazine,perhydrooxazepine, perhydrooxadiazepine, tetrahydrothiadiazole(thiadiazolidine), tetrahydrothiazine, tetrahydrothiadiazine,perhydrothiazepine, perhydrothiadiazepine, morpholine, thiomorpholine,oxathiane, perhydrobenzofuran, perhydroisobenzofuran,perhydrobenzothiophene, perhydroisobenzothiophene, perhydroindazole,perhydroquinoline, perhydroisoquinoline, perhydrophthalazine,perhydronaphthyridine, perhydroquinoxaline, perhydroquinazoline,perhydrocinnoline, perhydrobenzoxazole, perhydrobenzothiazole,perhydrobenzimidazole, perhydrocarbazole, perhydro-beta-carboline,perhydroacridine, perhydrodibenzofuran, perhydrodibenzothiophene,dioxolane, dioxane, dithiolane, dithiane etc.

Ring B is preferably a “nitrogen-containing heterocycle which may have asubstituent(s)”. The “nitrogen-containing heterocycle” represents amonocyclic, bicyclic or tricyclic heterocycle which contains at leastone nitrogen atom and may further contain 1 to 3 hetero atoms selectedfrom nitrogen, oxygen and sulfur atoms. The “nitrogen-containingheterocyclic ring” includes, for example, a “5- to 15-memberednitrogen-containing unsaturated monocyclic, bicyclic or tricyclicheterocycle” or a “5- to 15-membered nitrogen-containing saturatedmonocyclic, bicyclic or tricyclic heterocycle” etc. The “5- to15-membered nitrogen-containing unsaturated monocyclic, bicyclic ortricyclic heterocycle” includes, for example, pyrrole, imidazole,triazole, tetrazole, pyrazole, pyridine, pyrazine, pyrimidine,pyridazine, triazine, azepine, diazepine, oxazole, isoxazole, thiazole,isothiazole, furazan, oxadiazole, oxazine, oxadiazine, oxazepine,oxadiazepine, thiadiazole, thiazine, thiadiazine, thiazepine,thiadiazepine, indole, isoindole, indolizine, indazole, quinoline,isoquinoline, quinolizine, purine, phthalazine, pteridine,naphthyridine, quinoxaline, quinazoline, cinnoline, benzoxazole,benzothiazole, benzimidazole, benzoxazepine, benzoxadiazepine,benzothiazepine, benzothiadiazepine, benzazepine, benzodiazepine,benzofurazan, benzothiadiazole, benzotriazole, carbazole,beta-carboline, acridine, phenazine, phenothiazine, phenoxazine,phenanthridine, phenanthroline, perimidine, pyrroline, imidazoline,triazoline, tetrazoline, pyrazoline, dihydropyridine,tetrahydropyridine, dihydropyrazine, tetrahydropyrazine,dihydropyrimidine, tetrahydropyrimidine, dihydropyridazine,tetrahydropyridazine, tetrahydrotriazine, dihydroazepine,tetrahydroazepine, dihydrodiazepine, tetrahydrodiazepine,dihydrooxazole, dihydroisoxazole, dihydrothiazole, dihydroisothiazole,dihydrofurazan, dihydrooxadiazole, dihydrooxazine, dihydrooxadiazine,dihydrooxazepine, tetrahydrooxazepine, dihydrooxadiazepine,tetrahydrooxadiazepine, dihydrothiadiazole, dihydrothiazine,dihydrothiadiazine, dihydrothiazepine, tetrahydrothiazepine,dihydrothiadiazepine, tetrahydrothiadiazepine, indoline, isoindoline,dihydroindazole, dihydroquinoline, tetrahydroquinoline,dihydroisoquinoline, tetrahydroisoquinoline, dihydrophthalazine,tetrahydrophthalazine, dihydronaphthyridine, tetrahydronaphthyridine,dihydroquinoxaline, tetrahydroquinoxaline, dihydroquinazoline,tetrahydroquinazoline, dihydrocinnoline, tetrahydrocinnoline,dihydrobenzoxazine, dihydrobenzothiazine, pyrazinomorpholine,dihydrobenzoxazole, dihydrobenzothiazole, dihydrobenzimidazole,dihydrobenzazepine, tetrahydrobenzazepine, dihydrobenzodiazepine,tetrahydrobenzodiazepine, dihydrobenzoxazepine, tetrahydrobenzoxazepine,dihydrocarbazole, tetrahydrocarbazole, dihydro-beta-carboline,tetrahydro-beta-carboline, dihydroacridine, tetrahydroacridine,

The “5- to 15-membered nitrogen-containing saturated monocyclic,bicyclic or tricyclic heterocycle” includes, for example, pyrrolidine,imidazolidine, triazolidine, tetrazolidine, pyrazolidine, piperidine,piperazine, perhydropyrimidine, perhydropyridazine, perhydroazepine,perhydrodiazepine, perhydroazocine, tetrahydrooxazole (oxazolidine),tetrahydroisoxazole (isoxazolidine), tetrahydrothiazole (thiazolidine),tetrahydroisothiazole (isothiazolidine), tetrahydrofurazan,tetrahydrooxadiazole (oxadiazolidine), tetrahydrooxazine,tetrahydrooxadiazine, perhydrooxazepine, perhydrooxadiazepine,tetrahydrothiadiazole (thiadiazolidine), tetrahydrothiazine,tetrahydrothiadiazine, perhydrothiazepine, perhydrothiadiazepine,morpholine, thiomorpholine, perhydroindazole, perhydroquinoline,perhydroisoquinoline, perhydrophthalazine, perhydronaphthyridine,perhydroquinoxaline, perhydroquinazoline, perhydrocinnoline,perhydrobenzoxazole, perhydrobenzothiazole, perhydrobenzimidazole,perhydrocarbazole, perhydro-beta-carboline, perhydroacridine etc. The“Nitrogen-containing heterocyclic ring” is preferably a “6- to11-membered nitrogen-containing monocyclic or bicyclic heterocycle” etc.The “6- to 11-membered nitrogen-containing monocyclic or bicyclicheterocycle” includes, for example, a “6- to 11-membered unsaturatedmonocyclic or bicyclic heterocycle” or a “6- to 11-membered saturatedmonocyclic or bicyclic heterocycle” etc. The “6- to 11-memberedunsaturated monocyclic or bicyclic heterocycle” includes, for example,pyridine, pyrazine, pyrimidine, pyridazine, triazine, azepine,diazepine, oxazine, oxadiazine, oxazepine, oxadiazepine, thiazine,thiadiazine, thiazepine, thiadiazepine, indole, isoindole, indolizine,indazole, quinoline, isoquinoline, quinolizine, purine, phthalazine,pteridine, naphthyridine, quinoxaline, quinazoline, cinnoline,benzoxazole, benzothiazole, benzimidazole, benzoxazepine,benzoxadiazepine, benzothiazepine, benzothiadiazepine, benzazepine,benzodiazepine, benzofurazan, benzothiadiazole, benzotriazoledihydropyridine, tetrahydropyridine, dihydropyrazine,tetrahydropyrazine, dihydropyrimidine, tetrahydropyrimidine,dihydropyridazine, tetrahydropyridazine, tetrahydrotriazine,dihydroazepine, tetrahydroazepine, dihydrodiazepine,tetrahydrodiazepine, dihydrooxazine, dihydrooxadiazine,dihydrooxazepine, tetrahydrooxazepine, dihydrooxadiazepine,tetrahydrooxadiazepine, dihydrothiazine, dihydrothiadiazine,dihydrothiazepine, tetrahydrothiazepine, dihydrothiadiazepine,tetrahydrothiadiazepine, indoline, isoindoline, dihydroindazole,dihydroquinoline, tetrahydroquinoline, dihydroisoquinoline,tetrahydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine,dihydronaphthyridine, tetrahydronaphthyridine, dihydroquinoxaline,tetrahydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline,dihydrocinnoline, tetrahydrocinnoline, dihydrobenzoxazine,dihydrobenzothiazine, pyrazinomorpholine, dihydrobenzoxazole,dihydrobenzothiazole, dihydrobenzimidazole, dihydrobenzazepine,tetrahydrobenzazepine, dihydrobenzodiazepine, tetrahydrobenzodiazepine,dihydrobenzoxazepine, tetrahydrobenzoxazepine,

The “6- to 11-membered saturated monocyclic or bicyclic heterocycle”includes, for example, piperidine, piperazine, perhydropyrimidine,perhydropyridazine, perhydroazepine, perhydrodiazepine, perhydroazocine,perhydrooxazepine, perhydrooxadiazepine, tetrahydrothiadiazole(thiadiazolidine), tetrahydrothiazine, tetrahydrothiadiazine,perhydrothiazepine, perhydrothiadiazepine, morpholine, thiomorpholine,perhydroindazole, perhydroquinoline, perhydroisoquinoline,perhydrophthalazine, perhydronaphthyridine, perhydroquinoxaline,perhydroquinazoline, perhydrocinnoline, perhydrobenzoxazole,perhydrobenzothiazole, perhydrobenzimidazole etc. Ring B is morepreferably pyridine, quinoline, isoquinoline, pyrimidine, quinazoline,tetrahydroquinazoline,

Ring B may be substituted with 1 to 5 of R^(b) (R^(b) has the samemeaning as R³ which has the same meanings as described above.)

The “hydrocarbon group” in the “hydrocarbon group which may have asubstituent(s)” represented by Y includes, for example, C1-15 alkyl suchas methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl,pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl,tetradecyl, pentadecyl etc.; C2-10 alkenyl such as vinyl, allyl,2-methylallyl, 2-butenyl, 3-butenyl, 3-octenyl etc.; C2-10 alkynyl suchas ethynyl, 2-propynyl, 3-hexynyl etc.; cyclic hydrocarbon group (the“cyclic hydrocarbon” has the same meaning as “cyclic hydrocarbon”defined with above-mentioned ring B.); C7-16 aralkyl such as benzyl,phenylethyl etc.; (C3-8 cycloalkyl)-(C1-4 alkyl) such ascyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl,1-methyl-1-cyclohexylmethyl etc.

The “substituent” in the “hydrocarbon group which may have asubstituent(s)” include, for example, (1) nitro, (2) hydroxy, (3) oxo,(4) thioxo, (5) cyano, (6) carbamoyl, (7) aminocarbonyl substituted byC1-8 hydrocarbon (e.g. N-butylaminocarbonyl,N-cyclohexylmethylaminocarbonyl,N-butyl-N-cyclohexylmethylaminocarbonyl, N-cyclohexylaminocarbonyl,phenylaminocarbonyl etc.), (8) carboxy, (9) C1-4 alkoxy-carbonyl such asmethoxycarbonyl, ethoxycarbonyl etc., (10)sulfo, (11) halogen such asfluorine, chlorine, bromine or iodine, (12) C1-8 alkoxy such as methoxy,ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy,cyclohexylmethyloxy or benzyloxy etc., (13) C3-8 cycloalkoxy such ascyclohexyloxy etc., (14) phenoxy, (15) halogenophenoxy such as o-, m- orp-chlorophenoxy, or o-, m- or p-bromophenoxy etc., (16) C1-4 loweralkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio,n-butylthio, t-butylthio etc., (17) phenylthio, (18) C1-4 loweralkylsulfinyl such as methylsulfinyl or ethylsulfinyl etc., (19) C1-4lower alkylsulfonyl such as methylsulfonyl or ethylsulfonyl etc., (20)amino, (21) C1-6 lower acylamino such as acetylamino or propionylaminoetc., (22) primary or secondary amine substituted by hydrocarbon group(e.g. methylamino, ethylamino, n-propylamino, isopropylamino,n-butylamino, dimethylamino, diethylamino, cyclohexylamino,1-carbamoyl-2-cyclohexylethylamino, N-butyl-N-cyclohexylmethylamino orphenylamino etc.), (the “hydrocarbon group” has the same meanings asabove “hydrocarbon group” and may be substituted by oxo, amino orcarbamoyl etc.), (23) C1-4 lower acyl such as formyl or acetyl etc.,(24) benzoyl, (25) 5 or 6 membered hetero cyclic ring group such as 2-or 3-thienyl, 2- or 3-furyl, 3-, 4- or 5-pyrazolyl, 4-tetrahydropyranyl,2-, 4- or 5-thiazolyl, 3-, 4- or 5-isothiazolyl, 2-, 4- or 5-oxazolyl,3-, 4- or 5-isoxazolyl, 2-, 4- or 5-imidazolyl, 1,2,3- or1,2,4-triazolyl, 1H or 2H-tetrazolyl, 2-, 3- or 4-pyridyl, 2-, 4- or5-pyromidinyl, 3- or 4-pyridazinyl, quinolyl, isoquinolyl or indolyletc. which includes 1 to 4 hetero atoms selected from oxygen, sulfur andnitrogen besides carbon atom, and optionally has 1 to 4 substituentsselected from (a) e.g. halogen such as fluorine, chlorine, bromine oriodine, (b) hydrocarbon such as methyl, ethyl, propyl, isopropyl,benzyl, cyclohexyl, cyclohexylmethyl or cyclohexylethyl etc. optionallysubstituted by oxo or hydroxy etc., (the “hydrocarbon group” has thesame meanings as above “hydrocarbon group”), (c) halogenophenoxy such aso-, m- or p-chlorophenoxy, or o-, m- or p-bromophenoxy etc., and (d) oxoetc., (26) C1-10 haloalkyl such as difluoromethyl, trifluoromethyl,trifluoroethyl or trichloroethyl etc., (27) hydroxyimino, (28)alkyloxyimino such as methyloxyimino or ethyloxyimino etc., (29)sulfamoyl, (30) aminosulfonyl substituted by hydrocarbon (e.g.methylaminosulfonyl etc.), (31) aminosulfonyl substituted by hydrocarbonsubstituted by amino (e.g. dimethylaminoethylaminosulfonyl ordimethylaminopropylaminosulfonyl etc.), or (32) sulfonylaminosubstituted by hydrocarbon (e.g. methylsulfonylamino etc.) etc. The“hydrocarbon group which may have a substituent(s)” can have 1 to 5 ofsubstituents selected from above (1) to (32). If the “hydrocarbon group”is cycloalkyl, cycloalkenyl, aryl or aralkyl, it may be have 1 to 4 ofC1-4 lower alkyl such as methyl, ethyl, propyl, isopropyl or butyl etc.as substituent. When the number of substituents is two or more, eachsubstituent may be same or different.

The “heterocycle” in “heterocyclic group which may have asubstituent(s)” represented by Y has the same meaning as “heterocycle”defined in above-mentioned ring B. The “heterocycle” represented by Ymay be substituted with 1 to 5 of R³ (R³ has the same meaning asdescribed above.)

A protecting group of amino group in the “amino group which may beprotected” includes, for example, (1) hydrocarbon group which may have asubstituent(s), (2) NR¹R² (R¹ and R² have the same meanings as describedabove respectively.), (3) ring C optionally substituted with 1 to 5 ofR³ (ring C and R³ have the same meanings as described aboverespectively), (4)

(wherein all symbols have the same meanings as described above.) etc.The “hydrocarbon group which may have a substituent(s)” as the“protecting group” in the “amino group which may be protected”represented by Y has the same meaning as described above.

The “protecting group” in the “hydroxyl group which may be protected” orthe “mercapto group which may be protected” represented by Y has thesame meaning as the “protecting group” in the “amino group which may beprotected”.

Preferred as Y is, for example, amino group which may be protected etc.More preferred is

(wherein all symbols have the same meanings as described above.)

The “spacer containing 1 to 3 atoms as a main chain” represented by Gmeans a space formed by 1 to 3 continued atoms. In this case, the“number of atoms as a main chain” should be counted such that atoms as amain chain become minimum. The “spacer having from 1 to 3 atoms as amain chain” include, for example, a bivalent group comprising 1 to 3selected from methylene (—CH₂—) which may have 1 or 2 of substituents,nitrogen atom (—NH—) which may have some substituents, —CO—, —O—, —S—,—SO— and —SO₂—. In the case, the substituent of methylene and imino havethe same meanings as the “substituent” of above-described the“hydrocarbon group which may have a substituent(s)”. Specifically, it isincludes, for example, —CR¹⁰⁴R¹⁰⁵—, —NR¹⁰⁶—, —CO—, —O—, —S—, NR¹⁰⁶CO—,—CONR¹⁰⁶—, —NR¹⁰⁶COCR¹⁰⁴R¹⁰⁵—, —CONR¹⁰⁶CR¹⁰⁴R¹⁰⁵— (wherein R¹⁰⁴-R¹⁰⁶have the same meaning as the “substituent” of above-described the“hydrocarbon group which may have a substituent(s)”.) etc.

Preferred as G is, for example, a bond or spacer containing one atom asa main chain etc. More preferred as G is, for example, a bond ormethylene.

The “nitrogen-containing heterocycle” in the “4- to 7-memberednitrogen-containing heterocyclic group which may have a substituent(s)”represented by ring J refers to a monocyclic heterocycle which maycontain, in addition to the nitrogen atom indicated in ring J in formula(I), 1 to 3 hetero atoms selected from nitrogen, oxygen and sulfuratoms. The “4- to 7-membered nitrogen-containing heterocycle” includes,for example, a “4- to 7-membered nitrogen-containing unsaturatedmonocyclic heterocycle”, a “4- to 7-membered nitrogen-containingsaturated monocyclic heterocycle” and the like.

The “4- to 7-membered nitrogen-containing unsaturated monocyclicheterocycle” includes, for example, pyrrole, imidazole, triazole,tetrazole, pyrazole, pyrroline, imidazoline, triazoline, tetrazoline,pyrazoline, dihydropyridine, tetrahydropyridine, dihydropyrazine,tetrahydropyrazine, dihydropyrimidine, tetrahydropyrimidine,dihydropyridazine, tetrahydropyridazine, dihydroazepine,tetrahydroazepine, dihydrodiazepine, tetrahydrodiazepine,dihydrooxazole, dihydroisoxazole, dihydrothiazole, dihydroisothiazole,dihydrofurazan, dihydrooxadiazole, dihydrooxazine, dihydrooxadiazine,dihydrooxazepine, tetrahydrooxazepine, dihydrooxadiazepine,tetrahydrooxadiazepine, dihydrothiadiazole, dihydrothiazine,dihydrothiadiazine, dihydrothiazepine, tetrahydrothiazepine,dihydrothiadiazepine, tetrahydrothiadiazepine ring etc.

“4- to 7-membered nitrogen-containing saturated monocyclic heterocycle”includes, for example, azetidine, pyrrolidine, imidazolidine,triazolidine, tetrazolidine, pyrazolidine, piperidine, piperazine,perhydropyrimidine, perhydropyridazine, perhydroazepine,perhydrodiazepine, tetrahydrooxazole (oxazolidine), tetrahydroisoxazole(isoxazolidine), tetrahydrothiazole (thiazolidine),tetrahydroisothiazole (isothiazolidine), tetrahydrofurazan,tetrahydrooxadiazole (oxadiazolidine), tetrahydrooxazine,tetrahydrooxadiazine, perhydrooxazepine, perhydrooxadiazepine,tetrahydrothiadiazole (thiadiazolidine), tetrahydrothiazine,tetrahydrothiadiazine, perhydrothiazepine, perhydrothiadiazepine,morpholine, thiomorpholine etc.

Preferred as J is, for example, “4- to 7-membered nitrogen-containingsaturated monocyclic heterocycle”. More preferred as J is, for example,azetidine, pyrrolidine, piperidine or perhydroazepine etc.

Ring J may be substituted with 1 to 5 of R³ (R³ has a same meaning asdescribed above.)

The “hydrocarbon group which may have a substituent(s)” represented by Whas the same meaning as the “hydrocarbon group which may have asubstituent(s)” defined in above-mentioned Y.

The “heterocyclic group which may have a substituent(s)” represented byW has the same meaning as the “heterocyclic group which may have asubstituent(s)” defined in above-mentioned ring B.

Preferred as W is, for example, hydrogen atom or C1-8 hydrocarbon groupwhich may have a substituent(s). The “hydrocarbon group” has a samemeaning as described above. More preferred as W is, for example,hydrogen atom, methyl, isobutyl, 2-ethylbutyl, cyclohexylmethyl,cyclohexyl, benzyl or tetrahydropyran-4-yl etc.

The “5- to 10-membered nitrogen-containing saturated heterocyclic groupwhich may have a substituent(s), or a 5- to 10-memberednitrogen-containing heterocyclic group which has one double bond andwhich may have a substituent(s)” represented by ring A¹ in formula (I-1)include a monocyclic or bicyclic heterocycle which is fully saturated orcomprising one double bond and which may contain, in addition to thenitrogen atom indicated in ring A¹ in formula (I), 1 to 3 hetero atomsselected from nitrogen, oxygen and sulfur atoms. The “5- to 10-memberednitrogen-containing saturated heterocycle” includes, for example,pyrrolidine, imidazolidine, triazolidine, tetrazolidine, pyrazolidine,piperidine, piperazine, perhydropyrimidine, perhydropyridazine,perhydroazepine, perhydrodiazepine, perhydroazocine, tetrahydrooxazole(oxazolidine), tetrahydroisoxazole (isoxazolidine), tetrahydrothiazole(thiazolidine), tetrahydroisothiazole (isothiazolidine),tetrahydrofurazan, tetrahydrooxadiazole (oxadiazolidine),tetrahydrooxazine, tetrahydrooxadiazine, perhydrooxazepine,perhydrooxadiazepine, tetrahydrothiadiazole (thiadiazolidine),tetrahydrothiazine, tetrahydrothiadiazine, tetrahydrothiazepine,perhydrothiazepine, perhydrothiadiazepine, morpholine, thiomorpholine,perhydroindazole, perhydroquinoline, perhydroisoquinoline,perhydrophthalazine, perhydronaphthyridine, perhydroquinoxaline,perhydroquinazoline, perhydrocinnoline, perhydrobenzoxazole,perhydrobenzothiazole, perhydrobenzimidazole, perhydroazonine,perhydroazecine, perhydrodiazocine, perhydrodiazonine,perhydrodiazecine, perhydroindole, perhydroisoindole,azabicyclo[3.2.2]nonane, azabicyclo[3.3.2]decane,azabicyclo[2.2.2]octane etc.

“5- to 10-membered nitrogen-containing heterocyclic group which has onedouble bond” includes, for example, pyrroline, imidazoline, triazoline,tetrazoline, pyrazoline, tetrahydropyridine, tetrahydropyrazine,tetrahydropyrimidine, tetrahydropyridazine, tetrahydroazepine,tetrahydrodiazepine, dihydrooxazole, dihydroisoxazole, dihydrothiazole,dihydroisothiazole, dihydrofurazan, dihydrooxadiazole, dihydrooxazine,dihydrooxadiazine, tetrahydrooxazepine, tetrahydrooxadiazepine,dihydrothiadiazole, dihydrothiazine, dihydrothiadiazine,tetrahydrothiazepine, tetrahydrothiadiazepine, hexahydroazocine,hexahydroazonine, hexahydrodiazonine, hexahydrodiazonine,octahydroazecine, octahydrodiazecine etc.

Preferred as ring A¹ is, for example, 5- to 10-memberednitrogen-containing saturated heterocycle etc. More preferred is, forexample, perhydroazepine, perhydroazocine, piperidine or

Ring A¹ may be substituted with 1 to 5 of R^(a) (R^(a) has a samemeaning as R³, which has a same meaning as described above.)

The “6- to 11-membered nitrogen-containing monocyclic or bicyclicheterocycle” has a same meaning as described above. Preferred as ring B¹is, for example, pyridine, quinoline, isoquinoline, pyrimidine,quinazoline, tetrahydroquinazoline,

Ring B¹ may be substituted with 1 to 5 of R^(b) (R^(b) has a samemeaning as R³, which has a same meaning as described above.)

In formula (I-3) of the present invention, the 4- to 15-memberedmonocyclic, bicyclic or tricyclic heterocyclic group which contains atleast one nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1or 2 oxygen atoms and/or one sulfur atom represented by ring A² includes4- to 15-membered monocyclic, bicyclic or tricyclic heterocyclic arylwhich may be partially or fully saturated and which contains at leastone nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom.

The 4- to 15-membered monocyclic, bicyclic or tricyclic heterocyclicaryl which contains at least one nitrogen atom and may further contain 1to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfur atom.includes, for example, pyrrole, imidazole, triazole, tetrazole,pyrazole, azepine, diazepine, indole, isoindole, indazole, purine,benzimidazole, benzotriazole, carbazole, β-carboline, phenothiazine,phenoxazine, perimidine etc.

The 4- to 15-membered monocyclic, bicyclic or tricyclic heterocyclicaryl which is partially or fully saturated and which contains at leastone nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom includes, for example, aziridine,azetidine, pyrroline, pyrrolidine, imidazoline, imidazolidine,triazoline, triazolidine, tetrazoline, tetrazolidine, pyrazoline,pyrazolidine, dihydropyridine, tetrahydropyridine, piperidine,dihydropyrazine, tetrahydropyrazine, piperazine, dihydropyrimidine,tetrahydropyrimidine, perhydropyrimidine, dihydropyridazine,tetrahydropyridazine, perhydropyridazine, dihydroazepine,tetrahydroazepine, perhydroazepine, perhydroazocine, dihydrodiazepine,tetrahydrodiazepine, perhydrodiazepine, dihydrooxazole,tetrahydrooxazole (oxazolidine), dihydroisoxazole, tetrahydroisoxazole(isoxazolidine), dihydrothiazole, tetrahydrothiazole (thiazolidine),dihydroisothiazole, tetrahydroisothiazole (isothiazolidine),dihydrofurazan, tetrahydrofurazan, dihydrooxadiazole,tetrahydrooxadiazole (oxadiazolidine), dihydrooxazine,tetrahydrooxazine, dihydrooxadiazine, tetrahydrooxadiazine,dihydrooxazepine, tetrahydrooxazepine, perhydrooxazepine,dihydrooxadiazepine, tetrahydrooxadiazepine, perhydrooxadiazepine,dihydrothiadiazole, tetrahydrothiadiazole (thiadiazolidine),dihydrothiazine, tetrahydrothiazine, dihydrothiadiazine,tetrahydrothiadiazine, dihydrothiazepine, tetrahydrothiazepine,perhydrothiazepine, dihydrothiadiazepine, tetrahydrothiadiazepine,perhydrothiadiazepine, morpholine, thiomorpholine, indoline,isoindoline, dihydroindazole, perhydroindazole, dihydroquinoline,tetrahydroquinoline, perhydroquinoline, dihydroisoquinoline,tetrahydroisoquinoline, perhydroisoquinoline, dihydrophthalazine,tetrahydrophthalazine, perhydrophthalazine, dihydronaphthyridine,tetrahydronaphthyridine, perhydronaphthyridine, dihydroquinoxaline,tetrahydroquinoxaline, perhydroquinoxaline, dihydroquinazoline,tetrahydroquinazoline, perhydroquinazoline, dihydrocinnoline,tetrahydrocinnoline, perhydrocinnoline, dihydrobenzoxazine,dihydrobenzothiazine, pyrazinomorpholine, dihydrobenzoxazole,perhydrobenzoxazole, dihydrobenzothiazole, perhydrobenzothiazole,dihydrobenzimidazole, perhydrobenzimidazole, dihydrobenzazepine,tetrahydrobenzazepine, dihydrobenzodiazepine, tetrahydrobenzodiazepine,dihydrobenzoxazepine, tetrahydrobenzoxazepine, dihydrocarbazole,tetrahydrocarbazole, perhydrocarbazole, dihydroacridine,tetrahydroacridine, perhydroacridine, hexahydroazocine,hexahydroazonine, hexahydrodiazocine, hexahydrodiazonine,octahydroazecine, octahydrodiazecine, perhydroazonine, perhydroazecine,azaundecane, azadodecane, azamidecane, azatetradecane, azapentadecane,perhydrodiazocine, perhydrodiazonine, perhydrodiazecine, diazaundecane,diazadodecane, diazatridecane, diazatetradecane, diazapentadecane,perhydroindole, perhydroisoindole, perhydro-beta-carboline,perhydrophenazine, perhydrophenothiazine, perhydrophenoxazine,perhydrophenanthridine, perhydrophenanthrodine, perhydroperimidine etc.

In formula (I-3) in the present invention, the 5- to 15-memberedmonocyclic, bicyclic or tricyclic heterocyclic group which contains atleast one nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1or 2 oxygen atoms and/or one sulfur atom represented by ring B² includesa 5- to 15-membered monocyclic, bicyclic or tricyclic heterocyclic arylwhich may be partially or fully saturated and which contains at leastone nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom.

The 5- to 15-membered monocyclic, bicyclic or tricyclic heterocyclicaryl which contains at least one nitrogen atom and may further contain 1to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfur atomincludes, for example, pyrrole, imidazole, triazole, tetrazole,pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, triazine, azepine,diazepine, oxazole, isoxazole, thiazole, isothiazole, furazan,oxadiazole, oxazine, oxadiazine, oxazepine, oxadiazepine, thiadiazole,thiazine, thiadiazine, thiazepine, thiadiazepine, indole, isoindole,indolizine, indazole, quinoline, isoquinoline, quinolizine, purine,phthalazine, pteridine, naphthyridine, quinoxaline, quinazoline,cinnoline, benzoxazole, benzothiazole, benzimidazole, benzoxazepine,benzoxadiazepine, benzothiazepine, benzothiadiazepine, benzazepine,benzodiazepine, benzofurazan, benzothiadiazole, benzotriazole,carbazole, beta-carboline, acridine, phenazine, phenothiazine,phenoxazine, phenanthridine, phenanthroline, perimidine etc.

The 5- to 15-membered monocyclic, bicyclic or tricyclic heterocyclicaryl which is partially or fully saturated and which contains at leastone nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom includes, for example, pyrroline,pyrrolidine, imidazoline, imidazolidine, triazoline, triazolidine,tetrazoline, tetrazolidine, pyrazoline, pyrazolidine, dihydropyridine,tetrahydropyridine, piperidine, dihydropyrazine, tetrahydropyrazine,piperazine, dihydropyrimidine, tetrahydropyrimidine, perhydropyrimidine,dihydropyridazine, tetrahydropyridazine, perhydropyridazine,tetrahydrotriazine, dihydroazepine, tetrahydroazepine, perhydroazepine,dihydrodiazepine, tetrahydrodiazepine, perhydrodiazepine,dihydrooxazole, tetrahydrooxazole (oxazolidine), dihydroisoxazole,tetrahydroisoxazole (isoxazolidine), dihydrothiazole, tetrahydrothiazole(thiazolidine), dihydroisothiazole, tetrahydroisothiazole(isothiazolidine), dihydrofurazan, tetrahydrofurazan, dihydrooxadiazole,tetrahydrooxadiazole (oxadiazolidine), dihydrooxazine,tetrahydrooxazine, dihydrooxadiazine, tetrahydrooxadiazine,dihydrooxazine, dihydrooxazepine, tetrahydrooxazepine,perhydrooxazepine, dihydrooxadiazepine, tetrahydrooxadiazepine,perhydrooxadiazepine, dihydrothiadiazole, tetrahydrothiadiazole(thiadiazolidine), dihydrothiazine, tetrahydrothiazine,dihydrothiadiazine, tetrahydrothiadiazine, dihydrothiazepine,tetrahydrothiazepine, perhydrothiazepine, dihydrothiadiazepine,tetrahydrothiadiazepine, perhydrothiadiazepine, morpholine,thiomorpholine, indoline, isoindoline, dihydroindazole,perhydroindazole, dihydroquinoline, tetrahydroquinoline,perhydroquinoline, dihydroisoquinoline, tetrahydroisoquinoline,perhydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine,perhydrophthalazine, dihydronaphthyridine, tetrahydronaphthyridine,perhydronaphthyridine, dihydroquinoxaline, tetrahydroquinoxaline,perhydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline,perhydroquinazoline, dihydrocinnoline, tetrahydrocinnoline,perhydrocinnoline, dihydrobenzoxazine, dihydrobenzothiazine,pyrazinomorpholine, dihydrobenzoxazole, perhydrobenzoxazole,dihydrobenzothiazole, perhydrobenzothiazole, dihydrobenzimidazole,perhydrobenzimidazole, dihydrobenzazepine, tetrahydrobenzazepine,dihydrobenzodiazepine, tetrahydrobenzodiazepine, dihydrobenzoxazepine,tetrahydrobenzoxazepine, dihydrocarbazole, tetrahydrocarbazole,perhydrocarbazole, dihydro-beta-carboline, tetrahydro-beta-carboline,perhydro-beta-carboline, dihydroacridine, tetrahydroacridine,perhydroacridine,6,7,8,9-tetrahydro-5H-pyrido[4′,3′:4,5]pyrrolo[2,3-b]pyridine,2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole,6,7,8,9-tetrahydro-5H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine,

In formula (I-A) of the present invention, 4- to 15-membered monocyclic,bicyclic or tricyclic heterocycle which is saturated or has one doublebond and which contains at least one nitrogen atom and may furthercontain 1 to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfuratom by ring A^(A) includes, for example, azetidine, pyrroline,pyrrolidine, imidazoline, imidazolidine, triazoline, triazolidine,tetrazoline, tetrazolidine, pyrazoline, pyrazolidine,tetrahydropyridine, piperidine, tetrahydropyrazine, piperazine,tetrahydropyrimidine, perhydropyrimidine, tetrahydropyridazine,perhydropyridazine, tetrahydroazepine, perhydroazepine,tetrahydrodiazepine, perhydroazocine, perhydrodiazepine, dihydrooxazole,tetrahydrooxazole (oxazolidine), dihydroisoxazole, tetrahydroisoxazole(isoxazolidine), dihydrothiazole, tetrahydrothiazole (thiazolidine),dihydroisothiazole, tetrahydroisothiazole (isothiazolidine),dihydrofurazan, tetrahydrofurazan, dihydrooxadiazole,tetrahydrooxadiazole (oxadiazolidine), dihydrooxazine,tetrahydrooxazine, dihydrooxadiazine, tetrahydrooxadiazine,tetrahydrooxazepine, perhydrooxazepine, tetrahydrooxadiazepine,perhydrooxadiazepine, dihydrothiadiazole, tetrahydrothiadiazole(thiadiazolidine), dihydrothiazine, tetrahydrothiazine,dihydrothiadiazine, tetrahydrothiadiazine, tetrahydrothiazepine,perhydrothiazepine, tetrahydrothiadiazepine, perhydrothiadiazepine,morpholine, thiomorpholine, perhydroindazole, perhydroquinoline,perhydroisoquinoline, perhydrophthalazine, perhydronaphthyridine,perhydroquinoxaline, perhydroquinazoline, perhydrocinnoline,perhydrobenzoxazole, perhydrobenzothiazole, perhydrobenzimidazole,perhydrocarbazole, perhydroacridine, hexahydroazocine, hexahydroazonine,hexahydrodiazocine, hexahydrodiazonine, octahydroazecine,octahydrodiazecine, perhydroazonine, perhydroazecine, azaundecane,azadodecane, azamidecane, azatetradecane, azapentadecane,perhydrodiazocine, perhydrodiazonine, perhydrodiazecine, diazaundecane,diazadodecane, diazatridecane, diazatetradecane, diazapentadecane,perhydroindole, perhydroisoindole, perhydro-beta-carboline,perhydrophenazine, perhydrophenothiadine, perhydrophenoxadine,perhydrophenanthridine, perhydrophenanthroline, perhydroperimidine etc.

In formula (I-B) of the present invention, 7- to 15-membered monocyclic,bicyclic or tricyclic heterocycle which is saturated or contains onedouble bond and which contains at least one nitrogen atom and mayfurther contain 1 to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or onesulfur atom represented by ring A^(B) includes, for example,tetrahydroazepine, perhydroazecine, tetrahydrodiazepine,perhydrodiazepine, perhydroazocine, tetrahydrooxazepine,perhydrooxazepine, tetrahydrooxadiazepine, perhydrooxadiazepine,tetrahydrothiazepine, perhydrothiazepine, tetrahydrothiadiazepine,perhydrothiadiazepine, perhydroindazole, perhydroquinoline,perhydroisoquinoline, perhydrophthalazine, perhydronaphthyridine,perhydroquinoxaline, perhydroquinazoline, perhydrocinnoline,perhydrobenzoxazole, perhydrobenzothiazole, perhydrobenzimidazole,perhydrocarbazole, perhydroacridine, hexahydroazocine, hexahydroazonine,hexahydrodiazocine, hexahydrodiazonine, octahydroazecine,octahydrodiazecine, perhydroazonine, perhydroazecine, azaundecane,azadodecane, azamidecane, azatetradecane, azapentadecane,perhydrodiazocine, perhydrodiazonine, perhydrodiazecine, diazaundecane,diazadodecane, diazatridecane, diazatetradecane, diazapentadecane,perhydroindole, perhydroisoindole, perhydro-beta-carbo line,perhydrophenazine, perhydrophenothiadine, perhydrophenoxadine,perhydrophenanthridine, perhydrophenanthroline, perhydroperimidine etc.

The bicyclic heterocycle represented by above-described A² in formula(I-3), A^(A) in formula (I-A) or A^(B) in formula (I-B) includes abridged bicyclic heterocycle. The bridged bicyclic heterocycle includes,for example, azabicyclo[3.2.2]nonane, azabicyclo[3.3.2]decane,azabicyclo[2.2.2]octane, azabicyclo[3.3.3]undecane,azabicyclo[4.3.3]dodecane, azabicyclo[4.4.3]tridecane,azabicyclo[4.4.4]tetradecane etc. The bridged bi-heterocyclic ring mayhave one double bond.

In formula (I-B) of the present invention, ring B^(B) is pyrimidine or1,3,5-triazine that may be fused with ring Z.

In the present invention, the C5-10 monocyclic or bicyclic carbocyclerepresented by ring Z includes, for example, cyclopentene, cyclohexene,cycloheptene, cyclooctene, cyclononene, cyclodecene, cyclopentadiene,cyclohexadiene, cycloheptadiene, cyclooctadiene, benzene, pentalene,azulene, indene, indan, naphthalene, dihydronaphthalene,tetrahydronaphthalene etc.

In the present invention, the 5- to 10-membered monocyclic or bicyclicheterocycle which may contain 1 or 2 nitrogen atoms, one oxygen atomand/or one sulfur atom represented by ring Z includes a 5- to10-membered mono- or bi-heterocyclic aryl which may be partiallysaturated and which may contain 1 or 2 nitrogen atoms, one oxygen atomand/or one sulfur atom.

The 5- to 10-membered mono- or bi-heterocyclic aryl which may contain 1or 2 nitrogen atoms, one oxygen atom and/or one sulfur atom includes,for example, pyrrole, imidazole, triazole, pyrazole, pyridine, pyrazine,pyrimidine, pyridazine, azepine, diazepine, furan, pyran, oxepine,thiophene, thiopyran, thiepine, oxazole, isoxazole, thiazole,isothiazole, furazan, oxadiazole, oxazine, oxadiazine, oxazepine,oxadiazepine, thiadiazole, thiazine, thiadiazine, thiazepine,thiadiazepine, indole, isoindole, indolizine, benzofuran, isobenzofuran,benzothiophene, isobenzothiophene, dithianaphthalene, indazole,quinoline, isoquinoline, quinolizine, purine, phthalazine, pteridine,naphthyridine, quinoxaline, quinazoline, cinnoline, benzoxazole,benzothiazole, benzimidazole, chromene, benzofurazan, benzothiadiazole,benzotriazole ring etc.

The 5- to 10-membered mono- or bi-heterocyclic aryl which is partiallysaturated and which may contain 1 or 2 nitrogen atoms, one oxygen atomand/or one sulfur atom includes, for example, pyrroline, imidazoline,pyrazoline, dihydropyridine, tetrahydropyridine, dihydropyrazine,tetrahydropyrazine, dihydropyrimidine, tetrahydropyrimidine,dihydropyridazine, tetrahydropyridazine, dihydroazepine,tetrahydroazepine, dihydrodiazepine, tetrahydrodiazepine, dihydrofuran,dihydropyran, dihydrooxepine, tetrahydrooxepine, dihydrothiophene,dihydrothiopyran, dihydrothiepine, tetrahydrothiepine, dihydrooxazole,dihydroisoxazole, dihydrothiazole, dihydroisothiazole, dihydrofurazan,dihydrooxadiazole, dihydrooxazine, dihydrooxadiazine, dihydrooxazepine,tetrahydrooxazepine, dihydrooxadiazepine, tetrahydrooxadiazepine,dihydrothiadiazole, dihydrothiazine, dihydrothiadiazine,dihydrothiazepine, tetrahydrothiazepine, dihydrothiadiazepine,tetrahydrothiadiazepine, dihydrooxazine, dihydrothiazine, oxathiane,indoline, isoindoline, dihydrobenzofuran, dihydroisobenzofuran,dihydrobenzothiophene, dihydroisobenzothiophene, dihydroindazole,dihydroquinoline, tetrahydroquinoline, dihydroisoquinoline,tetrahydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine,dihydronaphthyridine, tetrahydronaphthyridine, dihydroquinoxaline,tetrahydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline,dihydrocinnoline, tetrahydrocinnoline, benzoxathiane,dihydrobenzoxazine, dihydrobenzothiazine, pyrazinomorpholine,dihydrobenzoxazole, dihydrobenzothiazole, dihydrobenzimidazole,dioxaindan, benzodioxane, chroman, benzodithiolane, benzodithiane etc.

In the present invention, C1-8 alkylene represented by L meansmethylene, ethylene, propylene, butylene, pentylene, hexylene,heptylene, octylene or isomeric groups thereof.

In the present invention, C2-8 alkenylene represented by L meansethylene, propylene, butylene, pentylene, hexylene, heptylene, octyleneand isomeric groups thereof having one or two double bond(s),concretely, ethenylene, propenylene, butenylene, pentenylene,hexenylene, heptenylene, octenylene, hexadienylene, heptadienylene,octadienylene or isomeric groups thereof.

In the present invention, C2-8 alkynylene represented by L meansethylene, propylene, butylene, pentylene, hexylene, heptylene, octyleneand isomeric groups thereof having one triple bond, concretely,ethynylene, propynylene, butynylene, pentynylene, hexynylene,heptynylene, octynylene or isomeric groups thereof.

In the present invention, C3-8 carbocycle represented by L, R¹, R² andR⁴ means C3-8 monocyclic or bridged bicyclic carbocycle, for example,cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane,cyclooctane, cyclopentene, cyclohexene, cycloheptene, cyclooctene,cyclopentadiene, cyclohexadiene, cycloheptadiene, cyclooctadiene,benzene, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane etc.

In the present invention, C1-15 alkyl means methyl, ethyl, propyl,butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl,tridecyl, tetradecyl, pentadecyl or isomeric groups thereof.

In the present invention, C2-15 alkenyl means ethenyl, propenyl,butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl,undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl or isomericgroups thereof.

In the present invention, C2-15 alkynyl means ethynyl, propynyl,butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl,undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl or isomericgroups thereof.

In the present invention, the 4- to 15-membered heterocycle whichcontains at least one nitrogen atom and may further contain 1 or 2nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfur atom representedby ring C includes a 4- to 15-membered heterocyclic aryl which may bepartially or fully saturated and which contains at least one nitrogenatom and may further contain 1 or 2 nitrogen atoms, 1 or 2 oxygen atomsand/or one sulfur atom.

The 4- to 15-membered heterocyclic aryl which contains at least onenitrogen atom and may further contain 1 or 2 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom includes, for example, pyrrole,imidazole, triazole, pyrazole, pyridine, pyrazine, pyrimidine,pyridazine, azepine, diazepine, oxazole, isoxazole, thiazole,isothiazole, furazan, oxadiazole, oxazine, oxadiazine, oxazepine,oxadiazepine, thiadiazole, thiazine, thiadiazine, thiazepine,thiadiazepine, indole, isoindole, indolizine, indazole, quinoline,isoquinoline, quinolizine, phthalazine, naphthyridine, quinoxaline,quinazoline, cinnoline, benzoxazole, benzothiazole, benzimidazole,benzoxazepine, benzoxadiazepine, benzothiazepine, benzothiadiazepine,benzazepine, benzodiazepine, benzofurazan, benzothiadiazole,benzotriazole, carbazole, beta-carboline, acridine, phenazine, xanthene,phenothiazine, phenoxazine, phenoxathiin, phenanthridine,phenanthroline, perimidine etc.

The 4- to 15-membered heterocyclic aryl which is partially or fullysaturated and which contains at least one nitrogen atom and may furthercontain 1 or 2 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfuratom includes, for example, azetidine, pyrroline, pyrrolidine,imidazoline, imidazolidine, triazoline, triazolidine, tetrazoline,tetrazolidine, pyrazoline, pyrazolidine, dihydropyridine,tetrahydropyridine, piperidine, dihydropyrazine, tetrahydropyrazine,piperazine, dihydropyrimidine, tetrahydropyrimidine, perhydropyrimidine,dihydropyridazine, tetrahydropyridazine, perhydropyridazine,dihydroazepine, tetrahydroazepine, perhydroazepine, perhydroazocine,dihydrodiazepine, tetrahydrodiazepine, perhydrodiazepine,dihydrooxazole, tetrahydrooxazole (oxazolidine), dihydroisoxazole,tetrahydroisoxazole (isoxazolidine), dihydrothiazole, tetrahydrothiazole(thiazolidine), dihydroisothiazole, tetrahydroisothiazole(isothiazolidine), dihydrofurazan, tetrahydrofurazan, dihydrooxadiazole,tetrahydrooxadiazole (oxadiazolidine), dihydrooxazine,tetrahydrooxazine, dihydrooxadiazine, tetrahydrooxadiazine,dihydrooxazepine, tetrahydrooxazepine, perhydrooxazepine,dihydrooxadiazepine, tetrahydrooxadiazepine, perhydrooxadiazepine,dihydrothiadiazole, tetrahydrothiadiazole (thiadiazolidine),dihydrothiazine, tetrahydrothiazine, dihydrothiadiazine,tetrahydrothiadiazine, dihydrothiazepine, tetrahydrothiazepine,perhydrothiazepine, dihydrothiadiazepine, tetrahydrothiadiazepine,perhydrothiadiazepine, morpholine, thiomorpholine, oxathiane, indoline,isoindoline, dihydroindazole, perhydroindazole, dihydroquinoline,tetrahydroquinoline, perhydroquinoline, dihydroisoquinoline,tetrahydroisoquinoline, perhydroisoquinoline, dihydrophthalazine,tetrahydrophthalazine, perhydrophthalazine, dihydronaphthyridine,tetrahydronaphthyridine, perhydronaphthyridine, dihydroquinoxaline,tetrahydroquinoxaline, perhydroquinoxaline, dihydroquinazoline,tetrahydroquinazoline, perhydroquinazoline, dihydrocinnoline,tetrahydrocinnoline, perhydrocinnoline, benzoxathiane,dihydrobenzoxazine, dihydrobenzothiazine, pyrazinomorpholine,dihydrobenzoxazole, perhydrobenzoxazole, dihydrobenzothiazole,perhydrobenzothiazole, dihydrobenzimidazole, perhydrobenzimidazole,dihydrobenzazepine, tetrahydrobenzazepine, dihydrobenzodiazepine,tetrahydrobenzodiazepine, benzodioxepane, dihydrobenzoxazepine,tetrahydrobenzoxazepine, dihydrocarbazole, tetrahydrocarbazole,perhydrocarbazole, dihydroacridine, tetrahydroacridine,perhydroacridine, hexahydroazocine, hexahydroazonine,hexahydrodiazocine, hexahydrodiazonine, octahydroazecine,octahydrodiazecine, perhydroazonine, perhydroazecine, azaundecane,azadodecane, azamidecane, azatetradecane, azapentadecane,perhydrodiazocine, perhydrodiazonine, perhydrodiazecine, diazaundecane,diazadodecane, diazatridecane, diazatetradecane, diazapentadecane,perhydroindole, perhydroisoindole, perhydro-beta-carboline,perhydrophenazine, perhydrophenothiazine, perhydrophenoxazine,perhydrophenanthridine, perhydrophenanthrodine, perhydroperimidine etc.

In the present invention, the 5- to 15-membered monocyclic, bicyclic ortricyclic heterocycle which contains 1 to 4 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom represented by ring D and E includesa 5- to 15-membered monocyclic, bicyclic or tricyclic heterocyclic arylwhich may be partially or fully saturated and which contains 1 to 4nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfur atom. The 5- to15-membered monocyclic, bicyclic or tricyclic heterocyclic aryl whichcontains 1 to 4 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfuratom includes, for example, pyrrole, imidazole, triazole, tetrazole,pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, azepine,diazepine, furan, pyran, oxepine, thiophene, thiopyran, thiepine,oxazole, isoxazole, thiazole, isothiazole, furazan, oxadiazole, oxazine,oxadiazine, oxazepine, oxadiazepine, thiadiazole, thiazine, thiadiazine,thiazepine, thiadiazepine, indole, isoindole, indolizine, benzofuran,isobenzofuran, benzothiophene, isobenzothiophene, dithianaphthalene,indazole, quinoline, isoquinoline, quinolizine, purine, phthalazine,pteridine, naphthyridine, quinoxaline, quinazoline, cinnoline,benzoxazole, benzothiazole, benzimidazole, chromene, benzoxepine,benzoxazepine, benzoxadiazepine, benzothiepine, benzothiazepine,benzothiadiazepine, benzazepine, benzodiazepine, benzofurazan,benzothiadiazole, benzotriazole, carbazole, beta-carboline, acridine,phenazine, dibenzofuran, xanthene, dibenzothiophene, phenothiazine,phenoxazine, phenoxathiin, thianthrene, phenanthridine, phenanthroline,perimidine etc.

The 5- to 15-membered monocyclic, bicyclic or tricyclic heterocyclicaryl which is partially or fully saturated and which contains 1 to 4nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfur atom includes, forexample, pyrroline, pyrrolidine, imidazoline, imidazolidine, triazoline,triazolidine, tetrazoline, tetrazolidine, pyrazoline, pyrazolidine,dihydropyridine, tetrahydropyridine, piperidine, dihydropyrazine,tetrahydropyrazine, piperazine, dihydropyrimidine, tetrahydropyrimidine,perhydropyrimidine, dihydropyridazine, tetrahydropyridazine,perhydropyridazine, dihydroazepine, tetrahydroazepine, perhydroazepine,dihydrodiazepine, tetrahydrodiazepine, perhydrodiazepine,dihydrooxazole, tetrahydrooxazole (oxazolidine), dihydroisoxazole,tetrahydroisoxazole (isoxazolidine), dihydrothiazole, tetrahydrothiazole(thiazolidine), dihydroisothiazole, tetrahydroisothiazole(isothiazolidine), dihydrofurazan, tetrahydrofurazan, dihydrooxadiazole,tetrahydrooxadiazole (oxadiazolidine), dihydrooxazine,tetrahydrooxazine, dihydrooxadiazine, tetrahydrooxadiazine,dihydrooxazepine, tetrahydrooxazepine, perhydrooxazepine,dihydrooxadiazepine, tetrahydrooxadiazepine, perhydrooxadiazepine,dihydrothiadiazole, tetrahydrothiadiazole (thiadiazolidine),dihydrothiazine, tetrahydrothiazine, dihydrothiadiazine,tetrahydrothiadiazine, dihydrothiazepine, tetrahydrothiazepine,perhydrothiazepine, dihydrothiadiazepine, tetrahydrothiadiazepine,perhydrothiadiazepine, morpholine, thiomorpholine, oxathiane, indoline,isoindoline, dihydroindazole, perhydroindazole, dihydroquinoline,tetrahydroquinoline, perhydroquinoline, dihydroisoquinoline,tetrahydroisoquinoline, perhydroisoquinoline, dihydrophthalazine,tetrahydrophthalazine, perhydrophthalazine, dihydronaphthyridine,tetrahydronaphthyridine, perhydronaphthyridine, dihydroquinoxaline,tetrahydroquinoxaline, perhydroquinoxaline, dihydroquinazoline,tetrahydroquinazoline, perhydroquinazoline, dihydrocinnoline,tetrahydrocinnoline, perhydrocinnoline, benzoxathiane,dihydrobenzoxazine, dihydrobenzothiazine, pyrazinomorpholine,dihydrobenzoxazole, perhydrobenzoxazole, dihydrobenzothiazole,perhydrobenzothiazole, dihydrobenzimidazole, perhydrobenzimidazole,dihydrobenzazepine, tetrahydrobenzazepine, dihydrobenzodiazepine,tetrahydrobenzodiazepine, benzodioxepane, dihydrobenzoxazepine,tetrahydrobenzoxazepine, dihydrocarbazole, tetrahydrocarbazole,perhydrocarbazole, dihydroacridine, tetrahydroacridine, perhydroacridinering etc.

In the present invention, C3-15 monocyclic, bicyclic or tricycliccarbocycle represented by ring D and ring E includes C3-15 monocyclic,bicyclic or tricyclic carbocyclic aryl which may be saturated partiallyor fully, bicyclic heterocycle having spiro bond and bridged bicyclicheterocycle, for example, cyclopropane, cyclobutane, cyclopentane,cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane,cycloundecane, cyclododecane, cyclotridecane, cyclotetradecane,cyclopentadecane, cyclopentene, cyclohexene, cycloheptene, cyclooctene,cyclopentadiene, cyclohexadiene, cycloheptadiene, cyclooctadiene,benzene, pentalene, perhydropentalene, azulene, perhydroazulene, indene,perhydroindene, indan, naphthalene, dihydronaphthalene,teterahydronaphthalene, perhydronaphthalene, heptalene,perhydroheptalene, biphenylene, as-indacene, s-indacene, acenaphthylene,acenaphthene, fluorene, phenalene, phenanthrene, anthracene,spiro[4.4]nonane, spiro[4.5]decane, spiro[5.5]undecane,bicyclo[2.2.1]heptane, bicyclo[2.2.1]hept-2-ene, bicyclo[3.1.1]heptane,bicyclo[3.1.1]hept-2-ene, bicyclo[2.2.2]octane, bicyclo[2.2.2]oct-2-ene,adamantane, noradamantane ring etc.

In the present invention, C1-15 alkoxy which is the substituent of ringE means methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy,heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy,tridecyloxy, tetradecyloxy, pentadecyloxy and isomeric groups thereof.

In the present invention, mono(C1-8 alkyl)amino group which is thesubstituent of ring E means methylamino, ethylamino, propylamino,butylamino, pentylamino, hexylamino, heptylamino, octylamino andisomeric groups thereof.

In the present invention, di(C1-8 alkyl)amino group which is thesubstituent of ring E means amino group substituted by same or differenttwo C1-8 alkyl, for example, dimethylamino, diethylamino, dipropylamino,dibutylamino, dipentylamino, dihexylamino, diheptylamino, dioctylamino,ethylmethylamino, ethylpropylamino, methylpropylamino and isomericgroups thereof.

The “hydrocarbon group which may have substituent(s)” represented byR¹⁰¹ and R¹⁰² has the same meaning as the “hydrocarbon group which mayhave substituent(s)” defined in Y.

In the present invention, halogen atom is fluorine, chlorine, bromineand iodine.

In the present invention, the CXCR4-regulating agent includes, as amatter of course, an agonist and an antagonist. The agonist includes afull agonist, partial agonist and inverse agonist, while the antagonistincludes a full antagonist and partial antagonist.

Also, in the present invention, the CXCR4-regulating agent may be anycompound which has an affinity for CXCR4 by itself or in combinationwith a CXCR4 ligand (for example, SDF-1, gp120 and the like) or with HIVand which may have either an agonistic or antagonistic effect.

Thus, as used herein, the CXCR4-regulating agent may be any compoundcapable of inhibiting the binding between CXCR4 and an intrinsic ligand(for example, SDF-1) or HIV. Therefore, it may be an agonist orantagonist, preferably antagonist.

Unless otherwise specifically mentioned, all isomers are included in thepresent invention. For example, alkyl, alkoxy and alkylene includestraight chain and branched ones. Moreover, all of isomers due to doublebond, ring and fused ring (E-, Z-, cis- and trans-forms), isomers due topresence of asymmetric carbon(s), etc. (R-, S-, α- and β-configuration,enantiomer and diastereomer), optically active substances having opticalrotation (D-, L-, d- and l-forms), polar compound by chromatographicseparation (high-polar compound and low-polar compound), equilibriumcompounds, rotational isomers, a mixture thereof in any proportion and aracemic mixture are included in the present invention.

According to the present invention, unless otherwise indicated and as isapparent for those skilled in the art, symbol

indicates that it is bound to the opposite side of the sheet (namelyα-configuration), symbol

indicates that it is bound to the front side of the sheet (namelyβ-configuration), symbol

indicates that it is α-configuration, β-configuration or a mixturethereof, and symbol

indicates that it is a mixture of α-configuration and β-configuration.

The compound of the present invention can be converted into a salt byknown methods.

The salt is preferably water-soluble.

The salt of the present invention are, for example, salt with alkalinemetal (such as potassium, sodium and lithium), salt with alkaline earthmetal (such as calcium and magnesium), ammonium salt (such astetramethylammonium salt and tetrabutylammonium salt), salt with organicamine (such as triethylamine, methylamine, dimethylamine,cyclopentylamine, benzylamine, phenethylamine, piperidine,monoethanolamine, diethanolamine, tris(hydroxymethyl)methylamine,lysine, arginine and N-methyl-D-glucamine) and acid addition salt (suchas inorganic acid salt (e.g., hydrochloride, hydrobromide, hydroiodide,sulfate, phosphate and nitrate) and organic acid salt (e.g., acetate,trifluoroacetate, lactate, tartrate, oxalate, fumarate, maleate,benzoate, citrate, methanesulfonate, ethanesulfonate, benzenesulfonate,toluenesulfonate, isothionate, glucuronate and gluconate), etc.)

N-oxide means a compound of formula (I) which nitrogen is oxidized. Thecompounds of the present invention can be converted to N-oxide byarbitrary methods. Salt and N-oxide of the compound of the presentinvention include solvate, or solvate of salt with alkaline (earth)metal, of ammonium salt, of salt with organic amine and of acid additionsalt, of the compound of the present invention.

The solvate is preferably non toxic and water-soluble. The suitablesolvate is, for example, solvate of water or alcohol (e.g. ethanol).

A prodrug of the compound of formula (I) means a compound which isconverted to the compound of formula (I) by reaction with an enzyme,gastric acid or the like in the living body. For example, with regard toa prodrug of the compound of formula (I), when the compound of formula(I) has an amino group, compounds in which the amino group is, forexample, acylated, alkylated or phosphorylated (e.g., compounds in whichthe amino group of the compound of formula (I) is eicosanoylated,alanylated, pentylaminocarbonylated,(5-methyl-2-oxo-1,3-dioxolen-4-yl)methoxycarbonylated,tetrahydrofuranylated, pyrrolidylmethylated, pivaloyloxymethylated,acetoxymethylated, tert-butylated, etc.); when the compound of formula(I) has a hydroxyl group, compounds where the hydroxyl group is, forexample, acylated, alkylated, phosphorylated or borated (e.g., compoundsin which the hydroxyl group of the compound of formula (I) isacetylated, palmitoylated, propanoylated, pivaloylated, succinylated,fumarylated, alanylated or dimethylaminomethylcarbonylated); and thatthe carboxyl group of the compound of formula (I) is, for example,esterified or amidated (e.g., compounds in which the carboxyl group ofthe compound of formula (I) is made into ethyl ester, phenyl ester,phenylethyl ester, carboxymethyl ester, dimethylaminomethyl ester,pivaloyloxymethyl ester, ethoxycarbonyloxyethyl ester, phthalidyl ester,(5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl ester,cyclohexyloxycarbonylethyl ester or methylamide). Those compounds may beproduced by a known method per se. The prodrug of the compound offormula (I) may be either a hydrate or a non-hydrate.

In the compound of the present invention represented by formula (I-3),preferred ring A² is any compound which is 4- to 15-membered monocyclic,bicyclic or tricyclic heterocycle which contains at least one nitrogenatom and may further contain 1 to 3 nitrogen atoms, 1 or 2 oxygen atomsand/or one sulfur atom. More preferred is 5- to 10-membered monocyclicor bicyclic heterocycle, concretely, pyrrolidine, piperidine,morpholine, tetrahydropyridine, perhydroquinoline, perhydroisoquinoline,perhydrodiazepine, perhydroazepine, perhydroazocine, perhydroazonine,perhydroazecine, 2-azabicyclo[3.2.2]nonane, 3-azabicyclo[3.2.2]nonane,1-azabicyclo[2.2.2]octane or 2-azabicyclo[2.2.2]octane etc., and mostpreferred is piperidine or perhydroazepine etc.

In the present invention, R^(a) is all preferred and more preferred isC1-4 alkyl which may be substituted with ring D, OR¹¹, OCOR¹², NR¹⁴R¹⁵,NR¹⁶COR¹², NR¹⁶CONR¹⁴R¹⁵, COOR¹³, COR¹², CONR¹⁴R¹⁵ or ring D etc. Morepreferred is C1-4 alkyl, phenyl, benzyl, acetyl, benzyloxycarbonyl,hydroxy, ethoxycarbonyl, carbamoyl, piperidinyl or cyclohexyl etc.

In the compound of the present invention represented by formula (I-3),preferred ring B² is any compound which is 5- to 15-membered monocyclic,bicyclic or tricyclic heterocycle which contains at least one nitrogenatom and may further contain 1 to 3 nitrogen atoms, 1 or 2 oxygen atomsand/or one sulfur atom. More preferred is 6 membered heterocyclic ringwhich may be fused with ring Z and which contains 1 to 3 nitrigen atoms.

Preferred as the above-described 6 membered heterocyclic ring ispyridine, pyrazine, pyrimidine, triazine, piperidine, piperazine,tetrahydropyridine, tetrahydropyrazine, tetrahydropyrimidine,tetrahydrotriazine etc.

In the present invention, preferred ring Z is C5-7 monocyclic carbocycleor 5- to 7-membered monocyclic heterocycle etc.

In the present invention, preferred ring B² is ring B^(A1) or ringB^(A2). Moreover,

(wherein the upward arrow represents a binding position to ring A²; andthe right-downward arrow represents a binding position to the nitrogenatom bound to L.) etc. is also preferred.

In the present invention, R^(b) is all preferred, and more preferred isC1-4 alkyl which may be substituted with ring D, OR¹¹, OCOR¹², NR¹⁴R¹⁵,NR¹⁶COR¹², NR¹⁶CONR¹⁴R¹⁵, COOR¹³, COR¹², CONR¹⁴R¹⁵ or ring D etc. Morepreferred is C1-4 alkyl, phenyl, benzyl, acetyl, benzyloxycarbonyl,hydroxy, ethoxycarbonyl, carbamoyl, piperidinyl or cyclohexyl etc.

In the compound represented by formula (I-A) of the present invention,4- to 15-membered monocyclic, bicyclic or tricyclic heterocycle which issaturated or has one double bond and which contains at least onenitrogen atom and may further contain 1 to 3 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom is all preferred as ring A^(A), andparticularly preferred is 5- to 10-membered monocyclic or bicyclicheterocycle which is saturated or has one double bond and which containsat least one nitrogen atom and may further contain 1 to 3 nitrogenatoms, 1 or 2 oxygen atoms and/or one sulfur atom.

In the compound represented by formula (I-A) of the present invention,the ring described in ring B^(A1) and ring B^(A2) is all preferred asring B^(A). More preferred is

(wherein the upward arrow represents a binding position to ring A^(A);and the right-downward arrow represents a binding position to thenitrogen atom bound to L.) etc.

In the compound represented by formula (I-B) of the present invention,7- to 15-membered monocyclic, bicyclic or tricyclic heterocycle which issaturated or contains one double bond and which contains at least onenitrogen atom and may further contain 1 to 3 nitrogen atoms, 1 or 2oxygen atoms and/or one sulfur atom is all preferred as ring A^(B), andparticularly preferred is 7- to 10-membered monocyclic, bicyclic ortricyclic heterocycle which is saturated or contains one double bond andwhich contains at least one nitrogen atom and may further contain 1 to 3nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfur atom.

In the compound represented by formula (I-B) of the present invention,ring B^(B) is all preferred, and pyrimidine which may be fused with ringZ etc. is more preferred. Preferred ring Z is C5-7 monocyclic carbocycleor 5 to 7 membered monocyclic heterocycle etc.

In the present invention, L is all preferred. Bond, C1-6 alkylene orC3-8 carbocycle etc. is more preferred. Bond, C1-4 alkylene or C3-7carbocycle etc. is particularly preferred.

In the present invention, both NR¹R² and ring C are preferable as Q.

In the present invention, preferable as R¹ and R² among NR¹R²represented by Q is hydrogen atom, C1-12 alkyl substituted with R¹⁰,C2-12 alkenyl, or C1-12 alkyl or C2-12 alkenyl substituted with ring D.More preferable is hydrogen atom, methyl, ethyl, propyl, isobutyl, butylor methylthiopropyl etc.

In the present invention, preferable as ring C represented by Q isazetidine, pyrrolidine, morpholine, piperazine, thiomorpholine,perhydroazepine, perhydroazocine, perhydroazonine or perhydroazecineetc.

In the present invention, preferable as ring D is C3-10 carbocycle or 5-to 15-membered heterocycle etc. More preferable is benzene, benzofuran,benzothiophene, pyrazole, benzodioxole, tetrahydrobenzene, furan,thiazole, naphthalene, thiophene, cyclopropane, quinoline, pyridine orcyclohexane etc.

In the present invention, preferable as R³ is C1-10 alkyl, C2-10alkenyl, C2-10 alkynyl, C1-10 alkyl substituted with R¹⁰, COOR¹², OR¹¹,NR¹⁴R¹⁵, COR¹², CONR¹⁴R¹⁵ or ring E.

In the present invention, preferable as R¹⁰ among R³ is COOR¹², OR¹¹,NR¹⁴R¹⁵, COR¹², CONR¹⁴R¹⁵ or ring E.

In the present invention, R⁴ is all preferable. More preferable ishydrogen atom, C1-8 alkyl, phenyl, COR⁵ or COOR⁶.

In the compound represented by formula (I), compounds represented byformulae (I-1), (I-2), (I-3), (I-A) and (1-B) etc. are preferable.

Among the compound represented by formula (I-3), preferred compounds arecompounds represented by formula (IA-1)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IA-2)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IA-3)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IA-4)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IA-5)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IA-6)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IA-7)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IA-8)

(wherein all symbols have the same meanings as described above.),compounds represented by formula (IB)

(wherein all symbols have the same meanings as described above.), andcompounds represented by formula (IC)

(wherein all symbols have the same meanings as described above.)

Compounds represented in example and compounds represented below, saltsthereof, N-oxides thereof or solvates thereof, or prodrugs thereof areincluded as a specific compound of the present invention.

-   (1)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²,N²-dimethylethane-1,2-diamine,-   (2)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-(2-ethylbutyl)-N²-methylethane-1,2-diamine,-   (3)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-methyl-N²-nonylethane-1,2-diamine,-   (4)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-methyl-N²-[2-(methylsulfanyl)ethyl]ethane-1,2-diamine,-   (5)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-benzyl-N²-methylethane-1,2-diamine,-   (6)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-{-4-[3-(dimethylamino)propoxy]benzyl}-N²-methylethane-1,2-diamine,-   (7)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-methyl-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]ethane-1,2-diamine,-   (8)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-methylethane-1,2-diamine,-   (9)    4-azepan-1-yl-N-[(1-methylpyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (10)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)pyrrolidin-2-yl]methyl}-5,6,7,8-tetrahydroquinazolin-2-amine,-   (11)    4-azepan-1-yl-N-[(1-nonylpyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (12)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]pyrrolidin-2-yl}methyl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (13)    4-azepan-1-yl-N-[(1-benzylpyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (14)    4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)propoxy]benzyl}pyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (15)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-2-yl}methyl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (16)    4-azepan-1-yl-N-(pyrrolidin-2-ylmethyl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (17)    4-azepan-1-yl-N-[(1-methylpiperidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (18)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)piperidin-2-yl]methyl}-5,6,7,8-tetrahydroquinazolin-2-amine,-   (19)    4-azepan-1-yl-N-[(1-nonylpiperidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (20)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]piperidin-2-yl}methyl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (21)    4-azepan-1-yl-N-[(1-benzylpiperidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (22)    4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)propoxy]benzyl}piperidin-2-yl)methyl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (23)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-2-yl}methyl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (24)    4-azepan-1-yl-N-(piperidin-2-ylmethyl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (25)    4-azepan-1-yl-N-(1-methylpyrrolidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (26)    4-azepan-1-yl-N-[1-(2-ethylbutyl)pyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (27)    4-azepan-1-yl-N-(1-nonylpyrrolidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (28)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]pyrrolidin-3-yl}-5,6,7,8-tetrahydroquinazolin-2-amine,-   (29)    4-azepan-1-yl-N-(1-benzylpyrrolidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (30)    4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)propoxy]benzyl}pyrrolidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (31)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-3-yl}-5,6,7,8-tetrahydroquinazolin-2-amine,-   (32)    4-azepan-1-yl-N-pyrrolidin-3-yl-5,6,7,8-tetrahydroquinazolin-2-amine,-   (33)    4-azepan-1-yl-N-(1-methylpiperidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (34)    4-azepan-1-yl-N-[1-(2-ethylbutyl)piperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine,-   (35)    4-azepan-1-yl-N-(1-nonylpiperidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (36)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]piperidin-3-yl}-5,6,7,8-tetrahydroquinazolin-2-amine,-   (37)    4-azepan-1-yl-N-(1-benzylpiperidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (38)    4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)propoxy]benzyl}piperidin-3-yl)-5,6,7,8-tetrahydroquinazolin-2-amine,-   (39)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-3-yl}-5,6,7,8-tetrahydroquinazolin-2-amine,-   (40)    4-azepan-1-yl-N-piperidin-3-yl-5,6,7,8-tetrahydroquinazolin-2-amine,-   (41)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-methylcyclohexane-1,2-diamine,-   (42)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-(2-ethylbutyl)cyclohexane-1,2-diamine,-   (43)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-nonylpiperidine-2,3-diamine,-   (44)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-[2-(methylsulfanyl)ethyl]piperidin-2,3-diamine,-   (45)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-benzylpiperidine-2,3-diamine,-   (46)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-{-4-[3-(dimethylamino)propoxy]benzyl}piperidin-2,3-diamine,-   (47)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidine-2,3-diamine,-   (48)    N-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)cyclohexane-1,2-diamine,-   (49)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-methylcyclopentane-1,2-diamine,-   (50)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-(2-ethylbutyl)cyclopentane-1,2-diamine,-   (51)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-nonylcyclopentane-1,2-diamine,-   (52)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-[2-(methylsulfanyl)ethyl]cyclopentane-1,2-diamine,-   (53)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-benzylcyclopentane-1,2-diamine,-   (54)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-{-4-[3-(dimethylamino)propoxy]benzyl}cyclopentane-1,2-diamine,-   (55)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]cyclopentane-1,2-diamine,-   (56)    N-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)cyclopentane-1,2-diamine,-   (57)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine,-   (58)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-(2-ethylbutyl)-N²-methylethane-1,2-diamine,-   (59)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-methyl-N²-nonylethane-1,2-diamine,-   (60)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-methyl-N²-[2-(methylsulfanyl)ethyl]ethane-1,2-diamine,-   (61)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-benzyl-N²-methylethane-1,2-diamine,-   (62)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-{-4-[3-(dimethylamino)propoxy]benzyl}-N²-methylethane-1,2-diamine,-   (63)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-methyl-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]ethane-1,2-diamine,-   (64)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-methylethane-1,2-diamine,-   (65)    4-azepan-1-yl-N-[(1-methylpyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (66)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)pyrrolidin-2-yl]methyl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (67)    4-azepan-1-yl-N-[(1-nonylpyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (68)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]pyrrolidin-2-yl}methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (69)    4-azepan-1-yl-N-[(1-benzylpyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (70) 4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)prop    oxy]benzyl}pyrrolidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (71)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-2-yl}methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (72)    4-azepan-1-yl-N-(pyrrolidin-2-ylmethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (73)    4-azepan-1-yl-N-[(1-methylpiperidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (74)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)piperidin-2-yl]methyl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (75)    4-azepan-1-yl-N-[(1-nonylpiperidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (76)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]piperidin-2-yl}methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (77)    4-azepan-1-yl-N-[(1-benzylpiperidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (78) 4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)prop    oxy]benzyl}piperidin-2-yl)methyl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (79)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-2-yl}methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (80)    4-azepan-1-yl-N-(piperidin-2-ylmethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (81)    4-azepan-1-yl-N-(1-methylpyrrolidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (82)    4-azepan-1-yl-N-[1-(2-ethylbutyl)pyrrolidin-3-yl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (83)    4-azepan-1-yl-N-(1-nonylpyrrolidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (84)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]pyrrolidin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (85)    4-azepan-1-yl-N-(1-benzylpyrrolidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (86)    4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)propoxy]benzyl}pyrrolidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (87)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (88)    4-azepan-1-yl-N-pyrrolidin-3-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (89)    4-azepan-1-yl-N-(1-methylpiperidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (90)    4-azepan-1-yl-N-[1-(2-ethylbutyl)piperidin-3-yl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (91)    4-azepan-1-yl-N-(1-nonylpiperidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (92)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]piperidin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (93)    4-azepan-1-yl-N-(1-benzylpiperidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (94)    4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)propoxy]benzyl}piperidin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (95)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-3-yl}-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (96)    4-azepan-1-yl-N-piperidin-3-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine,-   (97)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-methylcyclohexane-1,2-diamine,-   (98)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-(2-ethylbutyl)cyclohexane-1,2-diamine,-   (99)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-nonylpiperidine-2,3-diamine,-   (100)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-[2-(methylsulfanyl)ethyl]piperidine-2,3-diamine,-   (101)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-benzylpiperidine-2,3-diamine,-   (102)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-{-4-[3-(dimethylamino)propoxy]benzyl}piperidine-2,3-diamine,-   (103)    N³-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidine-2,3-diamine,-   (104)    N-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)cyclohexane-1,2-diamine,-   (105)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-methylcyclopentane-1,2-diamine,-   (106)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-(2-ethylbutyl)cyclopentane-1,2-diamine,-   (107)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-nonylcyclopentane-1,2-diamine,-   (108)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-[2-(methylsulfanyl)ethyl]cyclopentane-1,2-diamine,-   (109)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-benzylcyclopentane-1,2-diamine,-   (110)    N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-{-4-[3-(dimethylamino)propoxy]benzyl}cyclopentane-1,2-diamine,

(111)N¹-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]cyclopentane-1,2-diamine,

-   (112)    N-(4-azepan-1-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)cyclopentane-1,2-diamine,-   (113)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine,-   (114)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-(2-ethylbutyl)-N²-methylethane-1,2-diamine,-   (115)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-methyl-N²-nonylethane-1,2-diamine,-   (116)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-methyl-N²-[2-(methylsulfanyl)ethyl]ethane-1,2-diamine,-   (117)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-benzyl-N²-methylethane-1,2-diamine,-   (118)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-{4-[3-(dimethylamino)propoxy]benzyl}-N²-methylethane-1,2-diamine,-   (119)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-methyl-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]ethane-1,2-diamine,-   (120)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-methylethane-1,2-diamine,-   (121)    4-azepan-1-yl-N-[(1-methylpyrrolidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (122)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)pyrrolidin-2-yl]methyl}-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (123)    4-azepan-1-yl-N-[(1-nonylpyrrolidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (124)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]pyrrolidin-2-yl}methyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (125)    4-azepan-1-yl-N-[(1-benzylpyrrolidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (126)    4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)propoxy]benzyl}pyrrolidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (127)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-2-yl}methyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (128)    4-azepan-1-yl-N-(pyrrolidin-2-ylmethyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (129)    4-azepan-1-yl-N-[(1-methylpiperidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (130)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)piperidin-2-yl]methyl}-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (131)    4-azepan-1-yl-N-[(1-nonylpiperidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (132)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]piperidin-2-yl}methyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (133)    4-azepan-1-yl-N-[(1-benzylpiperidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (134)    4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)propoxy]benzyl}piperidin-2-yl)methyl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (135)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-2-yl}methyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (136)    4-azepan-1-yl-N-(piperidin-2-ylmethyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (137)    4-azepan-1-yl-N-(1-methylpyrrolidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (138)    4-azepan-1-yl-N-[1-(2-ethylbutyl)pyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (139)    4-azepan-1-yl-N-(1-nonylpyrrolidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (140)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]pyrrolidin-3-yl}-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (141)    4-azepan-1-yl-N-(1-benzylpyrrolidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (142)    4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)propoxy]benzyl}pyrrolidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (143)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-3-yl}-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (144)    4-azepan-1-yl-N-pyrrolidin-3-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (145)    4-azepan-1-yl-N-(1-methylpiperidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (146)    4-azepan-1-yl-N-[1-(2-ethylbutyl)piperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (147)    4-azepan-1-yl-N-(1-nonylpiperidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (148)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]piperidin-3-yl}-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (149)    4-azepan-1-yl-N-(1-benzylpiperidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (150)    4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)propoxy]benzyl}piperidin-3-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (151)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-3-yl}-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (152)    4-azepan-1-yl-N-piperidin-3-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine,-   (153)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-methylcyclohexane-1,2-diamine,-   (154)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-(2-ethylbutyl)cyclohexane-1,2-diamine,-   (155)    N³-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-nonylpiperidine-2,3-diamine,-   (156)    N³-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-[2-(methylsulfanyl)ethyl]piperidine-2,3-diamine,-   (157)    N³-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-benzylpiperidine-2,3-diamine,-   (158)    N³-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-{4-[3-(dimethylamino)propoxy]benzyl}piperidine-2,3-diamine,-   (159)    N³-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidine-2,3-diamine,-   (160)    N-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)cyclohexane-1,2-diamine,-   (161)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-methylcyclopentane-1,2-diamine,-   (162)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-(2-ethylbutyl)cyclopentane-1,2-diamine,-   (163)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-nonylcyclopentane-1,2-diamine,-   (164)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-[2-(methylsulfanyl)ethyl]cyclopentane-1,2-diamine,-   (165)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-benzylcyclopentane-1,2-diamine,-   (166)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-{4-[3-(dimethylamino)propoxy]benzyl}cyclopentane-1,2-diamine,-   (167)    N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]cyclopentane-1,2-diamine,-   (168)    N-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)cyclopentane-1,2-diamine,-   (169)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine,-   (170)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-(2-ethylbutyl)-N²-methylethane-1,2-diamine,-   (171)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-methyl-N²-nonylethane-1,2-diamine,-   (172)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-methyl-N²-[2-(methylsulfanyl)ethyl]ethane-1,2-diamine,-   (173)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-benzyl-N²-methylethane-1,2-diamine,-   (174)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-{4-[3-(dimethylamino)propoxy]benzyl}-N²-methylethane-1,2-diamine,-   (175)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-methyl-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]ethane-1,2-diamine,-   (176)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-methylethane-1,2-diamine,-   (177)    4-azepan-1-yl-N-[(1-methylpyrrolidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (178)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)pyrrolidin-2-yl]methyl}-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (179)    4-azepan-1-yl-N-[(1-nonylpyrrolidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (180)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]pyrrolidin-2-yl}methyl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (181)    4-azepan-1-yl-N-[(1-benzylpyrrolidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (182)    4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)propoxy]benzyl}pyrrolidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (183)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-2-yl}methyl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (184)    4-azepan-1-yl-N-(pyrrolidin-2-ylmethyl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (185)    4-azepan-1-yl-N-[(1-methylpiperidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (186)    4-azepan-1-yl-N-{[1-(2-ethylbutyl)piperidin-2-yl]methyl}-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (187)    4-azepan-1-yl-N-[(1-nonylpiperidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (188)    4-azepan-1-yl-N-({1-[2-(methylsulfanyl)ethyl]piperidin-2-yl}methyl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (189)    4-azepan-1-yl-N-[(1-benzylpiperidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (190) 4-azepan-1-yl-N-[(1-{4-[3-(dimethylamino)prop    oxy]benzyl}piperidin-2-yl)methyl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (191)    4-azepan-1-yl-N-({1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-2-yl}methyl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (192)    4-azepan-1-yl-N-(piperidin-2-ylmethyl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (193)    4-azepan-1-yl-N-(1-methylpyrrolidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (194)    4-azepan-1-yl-N-[1-(2-ethylbutyl)pyrrolidin-3-yl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (195)    4-azepan-1-yl-N-(1-nonylpyrrolidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (196)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]pyrrolidin-3-yl}-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (197)    4-azepan-1-yl-N-(1-benzylpyrrolidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (198) 4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)prop    oxy]benzyl}pyrrolidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (199)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]pyrrolidin-3-yl}-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (200)    4-azepan-1-yl-N-pyrrolidin-3-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (201)    4-azepan-1-yl-N-(1-methylpiperidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (202)    4-azepan-1-yl-N-[1-(2-ethylbutyl)piperidin-3-yl]-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (203)    4-azepan-1-yl-N-(1-nonylpiperidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (204)    4-azepan-1-yl-N-{1-[2-(methylsulfanyl)ethyl]piperidin-3-yl}-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (205)    4-azepan-1-yl-N-(1-benzylpiperidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (206) 4-azepan-1-yl-N-(1-{4-[3-(dimethylamino)prop    oxy]benzyl}piperidin-3-yl)-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (207)    4-azepan-1-yl-N-{1-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidin-3-yl}-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (208)    4-azepan-1-yl-N-piperidin-3-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-amine,-   (209)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-methylcyclohexane-1,2-diamine,-   (210)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-(2-ethylbutyl)cyclohexane-1,2-diamine,-   (211)    N³-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-nonylpiperidine-2,3-diamine,-   (212)    N³-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-[2-(methylsulfanyl)ethyl]piperidine-2,3-diamine,-   (213)    N³-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-benzylpiperidine-2,3-diamine,-   (214)    N³-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-{4-[3-(dimethylamino)propoxy]benzyl}piperidine-2,3-diamine,-   (215)    N³-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]piperidine-2,3-diamine,-   (216) N-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclo    hepta[d]pyrimidin-2-yl)cyclohexane-1,2-diamine,-   (217)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-methylcyclopentane-1,2-diamine,-   (218)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-(2-ethylbutyl)cyclopentane-1,2-diamine,-   (219)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-nonylcyclopentane-1,2-diamine,-   (220)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-[2-(methylsulfanyl)ethyl]cyclopentane-1,2-diamine,-   (221)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-benzylcyclopentane-1,2-diamine,-   (222)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-{4-[3-(dimethylamino)prop    oxy]benzyl}cyclopentane-1,2-diamine,-   (223)    N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²-[(3-phenyl-1H-pyrazol-4-yl)methyl]cyclopentane-1,2-diamine,    and-   (224)    N-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)cyclopentane-1,2-diamine.

Among the compounds represented by formula (I), more preferable arebelow-described compounds, salts thereof, N-oxides thereof or solvatesthereof, or prodrugs thereof.

-   (1) N-(4-azepan-1-ylpyrimidin-2-yl)ethane-1,2-diamine,-   (2)    N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine,-   (3)    4-azepan-1-yl-N-((3S)-1-cyclohexylpyrrolidin-3-yl)pyrimidin-2-amine,-   (4) 4-azepan-1-yl-N-((3S)-1-benzylpyrrolidin-3-yl)pyrimidin-2-amine,-   (5)    4-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)piperidin-3-yl]pyrimidin-2-amine,-   (6)    4-azepan-1-yl-N-[(3S)-1-cyclohexylpiperidin-3-yl]pyrimidin-2-amine,-   (7)    4-azepan-1-yl-N-[(3S)-1-tetrahydro-2H-pyran-4-ylpiperidin-3-yl]pyrimidin-2-amine,-   (8)    4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanol    and-   (9)    (3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclohexylcarbonyl)-1,4′-bipiperidin-3-amine.

Moreover besides the above-described compounds, below-describedcompounds, salts thereof, N-oxides thereof or solvates thereof, orprodrugs thereof are included as compounds represented by formula (II).

-   (1)    5-[(3-azetidin-1-ylphenyl)amino]-1-(2-hydroxycyclohexyl)piperidin-3-ol,-   (2)    1-(3-hydroxycyclohexyl)-5-[(6-pyrrolidin-1-ylpyrazin-2-yl)amino]piperidin-3-carboxylic    acid,-   (3)    1-butyl-5-[(6-piperidin-1-ylpyridin-2-yl)amino]piperidin-2-carboxylic    acid,-   (4)    3-{[5-(3-hydroxyazepan-1-yl)-1-methyl-1H-pyrrol-2-yl]amino}1-[4-(hydroxymethyl)cyclohexyl]piperidin-2-carboxylic    acid,-   (5)    1-[2-({4-hydroxy-1′-[(2-hydroxycyclohexyl)carbonyl]-1,4′-bipiperidin-3-yl}amino)-6-oxo-1,6-dihydropyrimidin-4-yl]proline,-   (6)    3-{[1-(3-aminopyrrolidin-1-yl)-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl]amino}-1′-[(3-hydroxycyclohexyl)carbonyl]-1,3′-bipiperidin-4-carboxylic    acid,-   (7)    2-(3-{[(4-{3-[(methylamino)carbonyl]piperidin-1-yl}-1,3,5-triazin-2-yl)amino]methyl}piperidin-1-yl)cyclohexanecarboxylic    acid,-   (8)    N-(1-{5-[(2-{1-[3-(hydroxymethyl)cyclohexyl]piperidin-3-yl}ethyl)amino]pyridazin-3-yl}piperidin-4-yl)acetamide,-   (9)    3-(3-hydroxy-5-{[(5-{3-[(methylsulfonyl)amino]azetidin-1-yl}pyridazin-3-yl)amino]methyl}piperidin-1-yl)cyclohexanecarboxylic    acid,-   (10)    1-(2-aminocyclohexyl)-5-[({6-[2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidin-4-yl}amino)methyl]piperidin-3-carboxylic    acid,-   (11)    2-amino-N-(3-{3-[(4-pyridin-2-ylquinolin-2-yl)amino]pyrrolidin-1-yl}cyclohexyl)cyclohexanecarboxamide,-   (12)    1-phenyl-N-[(1-pyridin-3-ylisoquinolin-3-yl)methyl]piperidin-3-amine,-   (13)    [4-(7-{[6-(4-hydroxyphenyl)pyridin-3-yl]amino}-1H-indol-2-yl)piperidin-1-yl]acetic    acid,-   (14)    2-(3-{4-[({2-[4-(cyclohexylsulfonyl)-3-methoxyphenyl]pyridin-4-yl}methyl)amino]-1H-indol-3-yl}piperidin-1-yl)-N-methylacetamide,-   (15)    {5-[4-{[2-(1-methylpiperidin-2-yl)-1,3-benzoxazol-4-yl]amino}-3,4-dihydroisoquinolin-2(1H)-yl]thien-2-yl}(phenyl)methanone,-   (16)    (6-{[1-({[7-(1-adamantylamino)-1-benzothien-2-yl]amino}methyl)cyclohexyl]amino}pyridin-3-yl)(thien-2-yl)methanone,-   (17)    4-[3-({6-[(1-hydroxycyclohexyl)methyl]-6-azaspiro[4.5]dec-8-yl}amino)-1-benzothien-4-yl]-N-methylpiperazine-1-carboxamide,-   (18)    2-{2-[({5-[4-(methylsulfonyl)piperazin-1-yl]pyrimidin-2-yl}amino)methyl]pyrrolidin-1-yl}-6-phenylnicotinic    acid,-   (19)    N-(1-{[[4-methoxy-4-(1,3-thiazol-2-yl)cyclohexyl](methyl)amino]methyl}cyclopropyl)-4-(5,6,7,8-tetrahydroquinolin-2-yl)-1H-imidazol-2-amine,-   (20) 5-(1-methyl-1,2,3,4-tetrahydroquinolin-8-yl)-N4    {5-[1-(3,4,5,6-tetrahydropyridin-2-yl)piperidin-4-yl]pyridin-3-yl}methyl)pyrazin-2-amine,-   (21)    1-[3-(4-{[4-(3,4-dihydroquinolin-1(2H)-yl)-5-fluoropyrimidin-2-yl]amino}piperidin-1-yl)phenyl]-2,2-dimethylpropan-1-one,-   (22)    1-(cyclohexylmethyl)-4-{[methyl(3-{[4-(3,4,5,6-tetrahydropyridin-2-ylamino)phenyl]amino}propyl)amino]methyl}cyclohexanol,-   (23)    4-(4-{[4-(4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl)pyrimidin-2-yl]amino}azepan-1-yl)cyclohexylmethylcarbamate,-   (24)    4-(3-{[4-(1-cyanocyclobutyl)pyrimidin-2-yl]amino}azetidin-1-yl)-2-(cyclopentyloxy)benzamide,-   (25)    1-({4-[4-({[4-(1-hydroxycyclopentyl)pyrimidin-2-yl]amino}methyl)piperidin-1-yl]tetrahydro-2H-pyran-4-yl}acetyl)piperidin-4-ol,-   (26)    1-(2-{[2-(2-tetrahydro-2H-pyran-4-ylpyridin-4-yl)-2-azabicyclo[2.2.2]oct-4-yl]amino}pyrimidin-4-yl)cycloheptanol,-   (27)    3-({4-[3-({6-[benzyl(ethyl)amino]pyridazin-3-yl}amino)-8-azabicyclo[3.2.1]oct-8-yl]-4-methylpiperidin-1-yl}carbonyl)phenol,-   (28)    N-({4-[{2-[(4-azepan-1-yl-5-phenyl-1,3-thiazol-2-yl)amino]ethyl}(methyl)amino]-1-hydroxycyclohexyl}methyl)morpholine-4-carboxamide,-   (29)    2-azepan-1-yl-5-{[1′-(pyridin-3-ylmethyl)-1,3′-bipiperidin-4-yl]amino}thiophene-3,4-dicarbonitrile,-   (30)    4-({3-[(2-pyrrolidin-1-ylphenyl)amino]pyrrolidin-1-yl}methyl)cyclohexanol,-   (31) methyl    4-(3-{[6-(3-azabicyclo[3.1.1]hept-3-yl)pyrimidin-4-yl]amino}piperidin-1-yl)butanoate,-   (32)    [2-({3-[(4-azocan-1-ylpyrimidin-2-yl)amino]azetidin-1-yl}methyl)phenyl](1-methylpiperidin-4-yl)methanone,-   (33)    N-(6-azonan-1-ylpyrimidin-4-yl)-1-[4-(tetrahydro-2H-pyran-4-yloxy)phenyl]azepan-3-amine,-   (34)    2-{3-[(4-azepan-1-ylquinazolin-2-yl)amino]pyrrolidin-1-yl}-1,3-thiazol-4-carboxamide,-   (35)    N¹-(4-azepan-1-ylthieno[3,2-d]pyrimidin-2-yl)-N⁴-cyclohexyl-N⁴-methylbutane-1,4-diamine,-   (36)    4-azepan-1-yl-N-(1-cyclopropylpiperidin-3-yl)-1,3-benzothiazol-2-amine,-   (37)    N-[1-(1-naphthylmethyl)azetidin-3-yl]-4-piperidin-1-yl-5,7-dihydrofuro[3,4-d]pyrimidin-2-amine,-   (38)    6-azepan-1-yl-N-[1-(4-phenoxyphenyl)piperidin-4-yl]-9H-purin-2-amine,-   (39)    4-azepan-1-yl-N-[1-(2-cyclopentylethyl)azepan-4-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine    and-   (40)    N-[4-({3-[(5-azepan-1-ylpyrazin-2-yl)amino]piperidin-1-yl}methyl)phenyl]acetamide.

Processes for the Preparation of the Compound of the Present Invention:

The compound of the present invention can be prepared by a method, suchas a method described below, a method according to that, or a methoddescribed in Examples.

In each method described below, a starting material can be used as asalt thereof. An example of the salt includes a salt of compound offormula (I) described above.

[1] Among a compound represented by formula (I)

(wherein all symbols have the same meanings as described above.), acompound in which Y is an amino group which may be protected, a hydroxylgroup which may be protected or a mercapto group which may be protected,i.e., a compound represented by formula (I-a)

(wherein Y¹ is an amino group which may be protected, a hydroxyl groupwhich may be protected or a mercapto group which may be protected andother symbols have the same meanings as described above.) can beprepared by reacting a compound represented formula (IIA)

(wherein X is a leaving group such as halogen atom, methanesulfonyloxy(OMs), p-toluenesulfonyloxy (OTs), trifluoromethanesulfonyloxy (OTf),alkylthio, alkylsulfinyl, alkylsulfonyl or hydroxysulfonyl, and othersymbols have the same meanings as described above.) with a compoundrepresented formula (III)

H—Y¹  (III)

(wherein all symbols have the same meanings as described above.), orreacting a compound represented by formula (IIB)

(wherein all symbols have the same meanings as described above.) with acompound represented by formula (IV)

(wherein all symbols have the same meanings as described above.)

The reaction of a compound represented by formula (IIA) and a compoundrepresented by formula (III) and the reaction of a compound representedby formula (IIB) and a compound represented by formula (IV) are knownand the reactions can be carried out by below described (A) or (B).

(A) It may be carried out in an organic solvent (e.g.N,N-dimethylformamide, N,N-dimethylacetoamide, dimethylsulfoxide,alcohol solvent (methanol, ethanol, benzylalcohol etc.)) or without asolvent at −78 to 200° C.(B) It may be carried out in an organic solvent (e.g. toluene, benzene)in the presence of a metallic salt (e.g. palladium acetate) and a ligand(e.g. tri(t-butyl)phosphine, dicyclohexyl(2-biphenyl)phosphine,2,2-bis(diphenylphosphino)-1,1′binaphthyl (BINAP)) by addition of a base(potassium phosphate, potassium carbonate, sodium t-butoxide, sodiumhydride, sodium amyl oxide etc.) at −78 to 200° C.[2] Among a compound represented by formula (I-a), a compound having atleast one primary or secondary amino group in ring A, ring B, Y¹ orsubstituents thereof, i.e., a compound represented by (I-a′)

(wherein ring A′, ring B′ and Y¹′ have the same meanings as ring A, ringB and Y¹, respectively, with the proviso that any of those orsubstituents thereof has at least one primary or secondary amino group.)can be prepared by a deprotection of a compound having at least oneprimary or secondary amino group which is protected in ring A, ring B,Y¹ or substituents thereof among a compound represented by formula(I-a), i.e., a compound represented by formula (I-X)

(wherein ring A^(X), ring B^(X) and Y^(1X) have the same meanings asring A, ring B and Y¹, respectively, with the proviso that any of thoseor substituents thereof has at least one primary or secondary aminogroup which is protected by protecting groups.) protected by protectinggroups.

The protective group of amino includes such as benzyloxycarbonyl,tert-butoxycarbonyl, allyloxycarbonyl (Alloc),1-methyl-1-(4-biphenyl)ethoxycarbonyl (Bpoc), trifluoroacetyl,9-fluorenylmethoxycarbonyl, benzyl (Bn), p-methoxybenzyl,benzyloxymethyl (BOM) and 2-(trimethylsilyl)ethoxymethyl (SEM) and thelike.

With regard to the protective group for amino, there is no particularlimitation to the above ones so far as it is a group which is able to beeasily and selectively detached. For example, a deprotection reactionmay be carried out by a method mentioned in “T. W. Greene, ProtectiveGroups in Organic Synthesis, John Wiley & Sons Inc, 1999”.

Deprotection reaction of a protective group for amino is known and itsexamples are as follows.

(1) a hydrolyzing reaction with an alkali;

(2) a deprotection reaction under an acidic condition;

(3) a deprotection reaction by hydrogenolysis; and

(4) a deprotection reaction using metal complex.

Those methods will be specifically illustrated as follows.

(1) A deprotection reaction using an alkali is carried out, for example,at the temperature of 0 to 40° C. using a hydroxide of alkaline metal(such as sodium hydroxide, potassium hydroxide and lithium hydroxide), ahydroxide of alkaline earth metal (such as barium hydroxide and calciumhydroxide), a carbonate (such as sodium carbonate and potassiumcarbonate), an aqueous solution thereof or a mixture thereof in anorganic solvent (such as methanol, tetrahydrofuran and 1,4-dioxane etc.alone, or a mixed solvent containing two or more solvents thereof at anoptional ratio).

(2) A deprotection reaction under an acidic condition (e.g. adeprotection of t-butoxycarbonyl or trityl etc.) is carried out, forexample, at the temperature of 0 to 100° C. in an organic acid (e.g.acetic acid, trifluoroacetic acid, methanesulfonic acid), an inorganicacid (e.g. hydrochloric acid and sulfuric acid) or a mixture thereof(such as hydrogen bromide/acetic acid) in water or an organic solvent(such as dichloromethane, chloroform, 1,4-dioxane, ethyl acetate andanisole etc.)

(3) A deprotection reaction by hydrogenolysis is carried out, forexample, at the temperature of 0 to 200° C. in a hydrogen atmosphere ofordinary pressure or high pressure or in the presence of ammoniumformate in the presence of a catalyst (such as palladium-carbon,palladium black, palladium hydroxide, platinum oxide and Raney nickel)in a solvent [such as an ether type (such as tetrahydrofuran,1,4-dioxane, dimethoxyethane and diethyl ether), an alcohol type (suchas methanol and ethanol), a benzene type (such as benzene and toluene),a ketone type (such as acetone and methyl ethyl ketone), a nitrile type(such as acetonitrile), an amide type (such as N,N-dimethylformamide),water, ethyl acetate, acetic acid or a mixed solvent comprising two ormore thereof].

(4) A deprotection reaction using a metal complex (e.g. a deprotectionof allyloxycarbonyl etc.) is carried out, for example, at thetemperature of 0 to 40° C. using a metal complex [such astetrakistriphenylphosphine palladium (0), bis(triphenylphosphine)palladium (II) dichloride, palladium (II) acetate andtris(triphenylphosphine) rhodium (I) chloride] in the presence orabsence of a phosphine agent (such as triphenyl phosphine) in thepresence of a trap reagent (such as tributyltin hydride, triethylsilane,dimedone, morpholine, diethylamine and pyrrolidine), an organic acid(such as acetic acid, formic acid and 2-ethylhexanoic acid) and/or anorganic acid salt (such as sodium 2-ethylhexanoate and potassium2-ethylhexanoate) in an organic solvent (such as dichloromethane,N,N-dimethylformamide, tetrahydrofuran, ethyl acetate, acetonitrile,dioxane and ethanol), water or a mixed solvent thereof.

Besides the above-mentioned method, for example, a deprotection reactionmay be carried out by a method mentioned in “T. W. Greene, ProtectiveGroups in Organic Synthesis, John Wiley & Sons Inc, 1999”.

As persons skilled in the art can easily understand that the aimedcompound of the present invention is able to be easily produced by usingappropriate ones among those deprotection reactions.

The reaction can be followed by conversion to a desired non-toxic saltthereof by a known method, if necessary.

[3]A compound represented by formula (I-a) can be prepared by areductive amination of a compound represented by formula (I-a′) whichprepared by the deprotection reaction of protecting groups of amino andcorresponding aldehyde or ketone.

The reductive amination is conventionally known and carried out, forexample, by reaction at a temperature of from 0 to 100° C. in an inertorganic solvent (dichloroethane, dichloromethane, N,N-dimethylformamide,etc. alone, or a mixed solvent containing two or more solvents thereofat an optional ratio) using a reducing agent (sodiumtriacetoxy-borohydride, sodium cyano-borohydride, tetrabutylammoniumborohydride, etc.), in the presence or absence of an organic acid(acetic acid, etc.) or in the presence or absence of a organic base(triethylamine, sodium hydrogencarbonate, etc.)

Among a compound represented by formula (I)

(wherein all symbols have the same meanings as described above.), acompound in which Y is hydrocarbon optionally having substituents orheterocyclic ring optionally having substituents, i.e., a compoundrepresented by formula (I-b)

(wherein M is hydrocarbon optionally having substituents or heterocyclicring optionally having substituents and other symbols have the samemeaning as described above.) can be prepared by reacting a compoundrepresented by formula (IIA)

(wherein all symbols have the same meanings as described above.) with acompound represented by formula (V)

(wherein all symbols have the same meanings as described above.) Thereaction is known. For example, it may be carried out in organic solvent(e.g. benzene, toluene, N,N-dimethylformamide, 1,4-dioxane,tetrahydrofuran, methanol, acetonitrile, dimethoxyethane, acetone) inpresence of a base (sodium ethylate, sodium hydroxide, potassiumhydroxide, triethylamine, sodium carbonate, sodium bicarbonate,potassium carbonate, cesium carbonate, thallium carbonate, tripotassiumphosphate, cesium fluoride, barium hydroxide, tetrabutylammoniumfluoride etc.)) or an aqueous solution thereof, or a mixture thereof,and catalyst (e.g. tetrakis(triphenylphosphine) palladium (Pd(PPh₃)₄),dichlorobis(triphenylphosphine) palladium (PdCl₂(PPh₃)₂), palladiumacetate (Pd(OAc)₂), palladium black,1,1′-bis(diphenylphosphinoferrocene)dichloropalladium (PdCl₂(dppf)₂),dichlorodiallyl palladium (PdCl₂(allyl)₂),iodephenylbis(triphenylphosphine)palladium (PhPdI(PPh₃)₂)) at roomtemperature to 120° C.[5] As apparent for those skilled in the art, when a compoundrepresented by formula (I-a) or a compound represented by formula (I-b)has hydroxy, carboxy, amino or mercapto which is not protected, thosecan be prepared by the reaction described from [1] to [4] and then by adeprotection of protective groups of hydroxy, carboxy, amino ormercapto.

The protective groups of amino are above-described.

The protective group of hydroxy includes, for example, methyl, trityl,methoxymethyl (MOM), 1-ethoxyethyl (EE), methoxyethoxymethyl (MEM),2-tetrahydropyranyl (THP), trimethylsilyl (TMS), triethylsilyl (TES),t-butyldimethylsilyl (TBDMS), t-butyldiphenylsilyl (TBDPS), acetyl (Ac),pivaloyl, benzoyl, benzyl (Bn), p-methoxybenzyl, allyloxycarbonyl(Alloc), and 2,2,2-trichloroethoxycarbonyl (Troc) etc.

The protective group of mercapto includes, for example, benzyl,methoxybenzyl, methoxymethyl (MOM), 2-tetrahydropyranyl (THP),diphenylmethyl and acetyl (Ac) etc.

The carboxyl-protective group includes, for example, methyl, ethyl,t-butyl, allyl, phenacyl and benzyl etc.

With regard to the protective group for carboxyl, hydroxyl, amino andmercapto, there is no particular limitation to the above ones so far asit is a group which is able to be easily and selectively detached. Forexample, a deprotection reaction may be carried out by a methodmentioned in “T. W. Greene, Protective Groups in Organic Synthesis, JohnWiley & Sons Inc, 1999”.

Deprotection reaction of a protective group for carboxyl, hydroxyl,amino or mercapto is known and its examples are as follows.

(1) a hydrolyzing reaction with an alkali;

(2) a deprotection reaction under an acidic condition;

(3) a deprotection reaction by hydrogenolysis;

(4) a deprotection reaction using metal complex;

(5) a deprotection reaction using an organic metal; and

(6) a deprotection reaction of silyl.

The methods from (1) to (4) can be carried out by above described methodand the methods of (5) and (6) will be specifically illustrated asfollows.

(5) A deprotection reaction using metal is carried out, for example, atthe temperature of 0 to 40° C. with or without ultrasonic wave in thepresence of powdery zinc in an acidic solvent (such as acetic acid, abuffer of pH 4.2 to 7.2 and a mixed solution of a solution thereof withan organic solvent such as tetrahydrofuran).

(6) A deprotection reaction of silyl is carried out, for example, at thetemperature of 0 to 40° C. using tetrabutylammonium fluoride in anorganic solvent miscible with water (such as tetrahydrofuran andacetonitrile etc.)

As persons skilled in the art can easily understand that the aimedcompound of the present invention is able to be easily produced by usingappropriate ones among those deprotection reactions.

The reaction can be followed by conversion to a desired non-toxic saltthereof by a known method, if necessary.

Besides the above-described methods, the compounds of the invention offormula (I) can be produced by using a combination of Examples describedin this description, or the conventionally known methods, for examplethe methods described in Comprehensive Organic Transformations: A Guideto Functional Group Preparations, 2nd Edition (Richard C. Larock, JohnWilley & Sons Inc, 1999).

In the above-described processes for the preparation, a compoundrepresented by formula (II) can be prepared using a compound representedby formula (VI)

(wherein all symbols have the same meanings as described above.) insteadof a compound represented by formula (IV)

(wherein all symbols have the same meanings as described above.)

In the present invention, the compounds of formulae (IIA) and (IIB)which are used as the starting material can be prepared by the methoddescribed in reaction scheme.

(in the reaction scheme, all symbols have the same meaning as describedabove.)

The compounds of formulae (III), (IV), (V), (VI) and (VII) used in thepresent invention are known compounds or can be prepared easily by knownmethods, for example the methods described in Comprehensive OrganicTransformations: A Guide to Functional Group Preparations, 2nd Edition(Richard C. Larock, John Willey & Sons Inc, 1999).

In each reaction of the specification, the reactions with heating, aswill be apparent to those skilled in the art, it may be carried withwater bath, oil bath, sand bath and microwave.

In each reaction of the specification, it may be used a solid phasereagent which is supported by polymer (for example, polystyrene,polyacrylamide, polypropylene or polyethyleneglycol etc.)

In each reaction of the specification, the obtained products may bepurified by conventional techniques. For example, the purification maybe carried out by distillation at atmospheric or reduced pressure, byhigh performance liquid chromatography with silica gel or magnesiumsilicate, by thin layer chromatography, by ion-exchange resin, byscavenger resin, by column chromatography, by washing or byrecrystallization. The purification may be done each reaction or afterseveral reactions.

Toxicity:

The toxicity of the compounds of the present invention represented byformulae (I) and (II), salts thereof, N-oxides thereof or solvatesthereof, or prodrugs thereof are very low and therefore the compoundsmay be considered safe for pharmaceutical use.

Application to Pharmaceuticals

Since the compounds of the present invention represented by formulae (I)and (II), salts, N-oxides or solvates thereof, or prodrugs thereof havea CXCR4-regulating effect, they are effective in treatment andprevention, for example, of an inflammatory/immune disease, allergicdisease, infectious disease, especially HIV infection and accompanyingdiseases, psychoneurotic disease, cerebral disease, cardiovasculardisease, metabolic disease and cancerous disease. In addition, it isalso useful in the in vitro or in vivo amplification of stem cells for agene therapy as well as in the regeneration medicine for the purpose ofperipheral blood stem cell recruitment and tissue repair. Among such aregeneration medicine, it is useful as a transplantation medicine agentemployed in bone marrow transplantation, peripheral blood stem celltransplantation and tissue repair.

The inflammatory/immune diseases include, for example, rheumatoidarthritis, arthritis, gout, transplanted organ rejection, graft versushost disease (GVHD), nephritis, psoriasis, rhinitis, conjunctivitis,multiple sclerosis, ulcerative colitis, Crohn's disease, shockaccompanied with bacterial infection, pulmonary fibrosis, systemicresponse syndrome (SIRS), acute pulmonary disorder, diabetes and thelike. The allergic diseases include, for example, asthma, atopicdermatitis, rhinitis, conjunctivitis and the like.

The infectious diseases, especially HIV infection and accompanyingdiseases, include, for example, acquired immunodeficiency syndrome(AIDS), candidosis, carinii pneumonia, cytomegalovirus retinitis,Kaposi's sarcoma, malignant lymphoma, AIDS encephalopathy, bacterialsepsis and the like.

The psychoneurotic diseases and the cerebral diseases include, forexample, dementia such as Alzheimer's disease, Parkinson's disease,cerebral stroke, cerebral infarction, epilepsy, schizophrenia,peripheral nervous disorder and the like.

The cardiovascular diseases include, for example, arteriosclorosis,ischemic reperfusion injury, hypertension, myocardial infarction, anginapectoris, cardiac insufficiency and the like.

The metabolic diseases include, for example, diabetes, osteoporosis,prostatic hypertrophy, pollakiuia and the like.

The cancerous diseases include, for example, mammary cancer, malignanttumor such as malignant lymphoma, cancer metastasis,post-radiotherapy/chemotherapy bone marrow suppression orthrombocytopenia and the like.

The compounds of the present invention of formulae (I) and (II), thesalts thereof, the N-oxides thereof or the solvates thereof, or theprodrugs thereof may be administered as a combined preparation bycombining with other pharmaceuticals for the purpose of

1) supplementing and/or enhancing of prevention and/or treatment effectof the compound,

2) improvement in pharmacokinetics and absorption and reduction of doseof the compound, and/or

3) reduction of side effect of the compound.

The combined preparation of the compounds of the present invention offormulae (I) and (II), the salts thereof, the N-oxides thereof or thesolvates thereof, or the prodrugs thereof with other pharmaceuticals maybe administered in a form of a compounded agent in which both componentsare compounded in a preparation or may be in a form in which they areadministered by means of separate preparations. The case ofadministration by means of separate preparations includes a simultaneousadministration and administrations with time difference. In the case ofadministrations with time difference, the compound of the presentinvention of formulae (I) and (II) may be firstly administered followedby administering the other pharmaceutical or the other pharmaceuticalmay be administered firstly followed by administering the compound ofthe present invention of formulae (I) and (II). Methods for each of theadministration are the same or different.

There is no particular limitation for the diseases showing preventionand/or treatment effect by the above-mentioned combined preparation, sofar as it is a disease in which the prevention and/or treatment effectof the compound of present invention of formulae (I) and (II) aresupplemented and/or enhanced.

Other agent for preventive and/or treating HIV infection and acquiredimmunodeficiency syndrome used for a combination with the compounds ofthe present invention of formulae (I) and (II), the salts thereof, theN-oxides thereof or the solvates thereof, or the prodrugs thereof arereverse transcriptase inhibitor, protease inhibitor, chemokine (such asCCR2, CCR3, CCR4, CCR5 and CXCR4) antagonist, fusion inhibitor, antibodyto surface antigen of HIV-1 and vaccine of HIV-1 etc.

Reverse transcriptase inhibitors are concretely (1)nucleoside/nucleotide reverse transcriptase inhibitors: zidovudine(brand name: Retrovir), didanosine (brand name: Videx), zalcitabine(brand name: HIVID), stavudine (brand name: Zerit), lamivudine (brandname: Epivir), abacavir (brand name: Ziagen), adefovir, dipivoxil,emtricitabine (brand name: Coviracil) or Tenofovir (brand name: Viread)etc. and (2) nonnucleoside reverse transcriptase inhibitors: nevirapine(brand name: Viramune), delavirdine (brand name: Rescriptor), efavirenz(brand name: Sustiva, Stocklin) or capravirine (AG1549) etc.

Protease inhibitors are concretely indinavir (brand name: Crixivan),ritonavir (brand name: Norvir), nelfinavir (brand name: Viracept),saquinavir (brand name: Invirase, Fortovase), amprenavir (brand name:Agenerase), lopinavir (brand name: Kaletra) or tipranavir etc.

As chemokine antagonists, internal ligand of chemokine receptor, itsderivatives, its non-peptide low molecular compound or antibody ofchemokine receptor are included.

The examples of internal ligand of chemokine receptor are concretely,MIP-1α, MIP-1β, RANTES, SDF-1α, SDF-1β, MCP-1, MCP-2, MCP-4, Eotaxin andMDC etc.

The derivatives of internal ligand are concretely, AOP-RANTES,Met-SDF-1α, Met-SDF-1βetc.

Antibodies of chemokine receptor are concretely, Pro-140 etc.

CCR2 antagonists are concretely written in specification of WO99/07351,WO99/40913, WO00/46195, WO00/46196, WO00/46197, WO00/46198, WO00/46199,WO00/69432 or WO00/69815 or in Bioorg. Med. Chem. Lett., 10, 1803 (2000)etc.

CCR3 antagonists are concretely written in specification of DE19837386,WO99/55324, WO99/55330, WO00/04003, WO00/27800, WO00/27835, WO00/27843,WO00/29377, WO00/31032, WO00/31033, WO00/34278, WO00/35449, WO00/35451,WO00/35452, WO00/35453, WO00/35454, WO00/35876, WO00/35877, WO00/41685,WO00/51607, WO00/51608, WO00/51609, WO00/51610, WO00/53172, WO00/53600,WO00/58305, WO00/59497, WO00/59498, WO00/59502, WO00/59503, WO00/62814,WO00/73327 or WO01/09088 etc.

CCR4 antagonists are concretely written in specification of WO02/030357or WO02/030358 etc.

CCR5 antagonists are concretely TAK-779, TAK-220, SCH-D, SCH-C,compounds written in specification of WO99/17773, WO99/32100,WO00/06085, WO00/06146, WO00/10965, WO00/06153, WO00/21916, WO00/37455,EP1013276, WO00/38680, WO00/39125, WO00/40239, WO00/42045, WO00/53175,WO00/42852, WO00/66551, WO00/66558, WO00/66559, WO00/66141, WO00/68203,JP-A-2000-309598, WO00/51607, WO00/51608, WO00/51609, WO00/51610,WO00/56729, WO00/59497, WO00/59498, WO00/59502, WO00/59503, WO00/76933,WO98/25605 or WO99/04794, WO99/38514 or in Bioorg. Med. Chem. Lett., 10,1803 (2000) etc.

CXCR4 antagonists are concretely AMD-3100, T-22, KRH-1120, KRH-1636,compounds written in specification of WO00/66112 etc.

Fusion Inhibitors are concretely, T-20 (Pentafuside) and T-1249 etc.

The examples of combination agents written above are intended toillustrate the present invention, but do not limit them.

The typical examples of the usual the dosage level in clinical trials ofreverse transcriptase inhibitors or protease inhibitors written beloware intended to illustrate the present invention, but do not limit them.

-   Zidovudine: 100 mg capsule, 200 mg per dose, 3 times per day; 300 mg    tablet, 300 mg per dose, twice per day;-   didanosine: 25-200 mg tablet, 125-200 mg per dose, twice per day;-   zalcitabine: 0.375-0.75 mg tablet, 0.75 mg per dose, 3 times per    day;-   stavudine: 15-40 mg capsule, 30-40 mg per dose, twice per day;-   lamivudine: 150 mg tablet, 150 mg per dose, twice per day;-   abacavir: 300 mg tablet, 300 mg per dose, twice per day;-   nevirapine: 200 mg tablet, 200 mg per dose, once per day for 14 days    and then twice per day;-   delavirdine: 100 mg tablet, 400 mg per dose, 3 times per day;-   efavirenz: 50-200 mg capsule, 600 mg per dose, once per day;-   indinavir: 200-400 mg capsule, 800 mg per dose, 3 times per day;-   ritonavir: 100 mg capsule, 600 mg per dose, twice per day;-   nelfinavir: 250 mg tablet, 750 mg per dose, 3 times per day;-   saquinavir: 200 mg capsule, 1,200 mg per dose, 3 times per day;-   amprenavir: 50-150 mg tablet, 1,200 mg per dose, twice per day.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formula (I) or(II) on asthma include antihistamines, antiallergic agents (chemotaxisinhibitors, histamine antagonists, thromboxane synthetase inhibitors,thromboxane antagonists, Th2 cytokine inhibitors), steroids,bronchodilators (xanthine derivatives, sympathetic nerve stimulators,parasympathetic nerve blockers), vaccinating agents, gold formulations,Chinese herb medicines, basic nonsteroidal antiinflammatory agents,5-lipoxygenase inhibitors, 5-lipoxygenase activating protein inhibitors,leukotriene synthesis inhibitors, prostaglandins, cannabinoid-2 receptorstimulators, antitussives, expectorants and the like.

The antihistamines include diphenhydramine, diphenylpyralinehydrochloride, diphenylpyraline teoclate, clemastine fumarate,dimenhydrinate, dl-chloropheniramine maleate, d-chloropheniraminemaleate, triprolidine hydrochloride, promethazine hydrochloride,alimemazine tartarate, isothipendyl hydrochloride, homochlorcyclizinehydrochloride, hydroxyzine, cyproheptadine hydrochloride, levocabastinehydrochloride, astemizol, bepotastine, desloratadine, TAK-427, ZCR-2060,NIP-530, mometason furoate, mizolastin, BP-294, andolast, auranofin,acribastine and the like.

The chemotaxis inhibitors among antiallergic agents include sodiumcromoglicate, tranilast, anlexanox, repirinast, ibudilast, pemirolastpotassium, tazanolast, nedocromil, cromogricate, Israpafant and thelike.

The histamine antagonists among antiallergic agent include ketotifenfumarate, azelastine hydrochloride, oxatomide, mequitazine, terfenadine,emedastine difumarate, epinastine hydrochloride, ebastine, cetirizinehydrochloride, olopatadine hydrochloride, loratadine, fexofenadine andthe like.

The thromboxane synthetase inhibitors among antiallergic agents include,for example, ozagrel hydrochloride, and imitrodast sodium and the like.

Examples of the thromboxane receptor antagonist among antiallergicinclude seratrodast, ramatroban, domitroban calcium dihydrate, andKT-2-962 and the like.

The Th2 cytokine inhibitors among antiallergic agents include suplatasttosilate and the like.

Examples of the steroids for external application include clobetasolpropionate, diflorasone acetate, fluocinonide, mometasone furoate,betamethasone dipropionate, betamethasone butyrate propionate,betamethasone valerate, difluprednate, budesonide, diflucortolonevalerate, amcinonide, halcinonide, dexamethasone, dexamethasonepropionate, dexamethasone valerate, dexamethasone acetate,hydrocortisone acetate, hydrocortisone butyrate, hydrocortisone butyratepropionate, deprodone propionate, prednisolone valerate acetate,fluocinolone acetonide, beclomethasone dipropionate, triamcinoloneacetonide, flumethasone pivalate, alclometasone dipropionate,clobetasone butyrate, beclomethasone propionate, fludroxycortide and thelike. The steroid preparations for internal use or injection includecortisone acetate, hydrocortisone, hydrocortisone sodium phosphate,hydrocortisone sodium succinate, fludrocortisone acetate, prednisolone,prednisolone acetate, prednisolone sodium succinate, prednisolonebutylacetate, prednisolone sodium phosphate, halopredone acetate, methylprednisolone, methyl prednisolone acetate, methyl prednisolone sodiumsuccinate, triamcinolone, triamcinolone acetate, triamcinoloneacetonide, dexamethasone, dexamethasone acetate, dexamethasone sodiumphosphate, dexamethasone palmitate, paramethasone acetate, betamethasoneand the like. The steroid preparations as an inhalant includebeclomethasone propionate, fluticasone propionate, budesonide,flunisolide, triamcinolone, ST-126P, ciclesonide, dexamethasonepalmitate, mometasone furoate, prasterone sulfate, deflazacort, methylprednisolone sreptanate, methylprednisolone sodium succinate and thelike.

The xanthine derivatives among bronchodilators include aminophylline,thoeophyline, doxophylline, cipamfylline, diprophilline, proxyphylline,cholinetheophylline and the like.

The sympathetic nerve stimulators among bronchodilators includeepinephrine, ephedrine hydrochloride, 1-methylephedrine hydrochloride,methoxyphenamine hydrochloride, isoproterenol sulfate, isoproterenolhydrochloride, ciprenaline sulfate, clorprenaline hydrochloride,trimetoquinol hydrochloride, salbutamol sulfate, terbutaline sulfate,hexoprenaline sulfate, tulobuterol hydrochloride, procaterolhydrochloride, fenoterol hydrobromide, formoterol fumarate, clenbuterolhydrochloride, mabuterol hydrochloride, salmeterol xinafoate,R,R-formoterol, tulobuterol, pirbuterol hydrochloride, ritodrinehydrochloride, bambuterol, dopexamin hydrochloride, meluadrine tartrate,AR-C68397, levosalbutamol, KUR-1246, KUL-7211, AR-C89855, and S-1319 andthe like.

The parasympathetic nerve blockers among bronchodilators includeipratropium bromide, flutropium bromide, oxitropium bromide, cimetropiumbromide, temiverine, tiotropium bromide revatropate (UK-112166) and thelike.

The vaccinating agents include paspat, asthremedin, broncasma berna,CS-560 and the like.

The gold formulations include sodium gold thiomalate and the like.

The basic nonsteroidal antiinflammatory agents include tiaramidehydrochloride, tinoridine hydrochloride, epirizole, emorfazone and thelike.

The 5-lipoxygenase inhibitors include zileuton, docebenone, piripost,SCH-40120, WY-50295, E-6700, ML-3000, TMK-688, ZD-2138, darbufelonemesylate, R-68151, E-6080, DuP-654, SC-45662, CV-6504, NE-11740,CMI-977, NC-2000, E-3040, PD-136095, CMI-392, TZI-41078, Orf-20485,IDB-18024, BF-389, A-78773, TA-270, FLM-5011, CGS-23885, A-79175,ETH-615 etc.

The 5-lipoxygenase activating protein inhibitors include MK-591, MK-886and the like.

The leukotriene synthesis inhibitors include auranofin, proglumetacinmaleate, L-674636, A-81834, UPA-780, A-93178, MK-886, REV-5901A,SCH-40120, MK-591, Bay-x-1005, Bay-y-1015, DTI-0026, amlexanox, E-6700and the like.

The prostaglandins (hereinafter abbreviated as “PG”) include PG receptoragonist, PG receptor antagonist and the like.

The PG receptor include PGE receptors (EP₁, EP₂, EP₃, EP₄), PGDreceptors (DP, CRTH2), PGF receptors (FP), PGI receptors (IP), TXreceptors (TP) and the like.

The antitussive agents include codeine phosphate, dihydrocodeinephosphate, oxymetebanol, dextromethorphan hydrobromide, pentoxyverinecitrate, dimemorfan phosphate, oxeladin citrate, clop erastine,benproberine phosphate, clofedanol hydrochloride, fominobenhydrochloride, noscapine, tipemidine hibenzate, eprazinonehydrochloride, plantago herb extract and the like.

The expectorants include foeniculated ammonia spirit, sodium hydrogencarbonate, potassium iodide, bromhexine hydrochloride, a cherry treeskin extract, carbocisteine, fudosteine, ambroxol hydrochloride,ambroxol hydrochloride sustained release capsule, methylcysteinehydrochloride, acetyl cysteine, ethyl L-cysteine hydrochloride,tyloxapol and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on atopic dermatitis (urticaria etc.) include steroids,nonsteroidal anti-inflammatory drugs (NSAID), immunosuppressant agents,prostaglandins, antiallergic agents, mediator releasing depressants,antihistamine drugs, forskolin preparations, phosphodiesteraseinhibitors, cannabinoid-2 receptor stimulators and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formula (I) onallergic diseases (allergic bronchopulmonary aspergillosis, allergiceosinophilic gastroenteritis and the like) include antiasthmatic agents,inhalation steroids, inhalation β2 stimulants, methylxanthine-basedantiasthmatic agents, antiallergic agents, antiinflammatory agents,anticholinergic agents and the like. Those which may also be exemplifiedinclude thromboxane antagonists, leukotriene antagonists, LTD4antagonists, PAF antagonists, phosphodiesterase inhibitors, β2 agonists,steroids, mediator release inhibitors, eosionophile chemotaxisinhibitors, macrolide antibiotics, immunosuppressants, desensitizing(allergen) injection formulations and the like.

The antiasthmatic agents include theophylline, procaterol, ketotifen,azelastine and the like.

The inhalation steroids include beclometasone, fluticasone, budesonideand the like.

The inhalation β2 stimulants include fenoterol, sabutamol, formoterol,salmeterol and the like.

The methylxanthine-based antiasthmatic agents include teophylline andthe like.

The antiallergic agents include ketotifen, terfenazine, azelastine,epinastine, suplatast, sodium cromoglicate and the like.

The antiinflammatory agents include diclofenac sodium, ibuprofen,indomethacin and the like.

The anticholinergic agents include ipratropium bromide, flutropiumbromide, oxitropium bromide, thiotropium bromide and the like.

The thromboxane antagonists include ozagrel, seratrodast and the like.

The leukotriene antagonists include pranlukas, montelukast, zafirlukast,zileuton and the like.

The macrolide-based antibiotics include erythromycin, roxithromycin andthe like.

The immunosuppressants include ciclosporin, tacroimus, FTY720 and thelike.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on hepatitis include liver hydrolysate formulations, polyenephosphatidylcholines, glycyrrizin formulations, protoporphyrin sodium,ursodesoxycholic acid, steroids, anticholinergic agents, antacids,propagermanium, lipid peroxidase inhibitors, mitochondorialbenzodiazepine receptor antagonists and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on arthritis and rheumatoid arthritis include metalloproteinaseinhibitors, immunosuppressants, nonsteroidal anti-inflammatory drugs(NSAID), steroids, prostaglandins, phosphodiesterase inhibitors,cannabinoid-2 receptor stimulants, disease modifying anti-rheumaticdrugs (slow-acting anti-rheumatic drug), antiinflammatory enzymepreparations, chondroprotective agents, T-cell inhibitors, TNFαinhibitors, prostaglandin synthase inhibitors, IL-6 inhibitors,interferon gamma agonists, IL-1 inhibitors and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on psoriasis include steroids, vitamin D derivatives and thelike.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on rhinitis include antihistamines, mediator releaseinhibitors, thoromboxane synthetase inhibitors, thromboxane A₂ receptorantagonists, leukotriene receptor antagonists, steroids, a adrenalinereceptor stimulants, xanthine derivatives, anticholinergic agents,prostaglandins, nitrogen monoxide synthetase inhibitors, β₂ adrenalinereceptor stimulants, phosphodiesterase inhibitors, cannabinoid-2receptor stimulants and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on conjunctivitis include leukotriene receptor antagonists,antihistamines, mediator release inhibitors, nonsteroidalantiinflammatory agents, prostaglandins, steroids, nitrogen monoxidesynthetase inhibitors, cannabinoid-2 receptor stimulants and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on multiple sclerosis include immunosuppressants, cannabinoid-2receptor stimulants and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on ulcerative colitis include mesalazine, salazosulfapyridine,digestive tract ulcer agents, anticholinergic agents, steroids,5-lipoxygenase inhibitors, antioxidants, LTB4 antagonists, localanesthetics, immunosuppressants, defensive factor promoters, MMPinhibitors, mitochondrual benzodiazepine receptor antagonists and thelike.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on complication of diabetes include sulfonylurea typehypoglycemic agents, biguanide preparations, alfa-glucosidaseinhibitors, fast-acting insulin secretion accelerators, insulinpreparations, PPAR agonists, insulin sensitizer without PPAR agonisticactivity, beta-3 adrenaline receptor activators, aldose reductaseinhibitors, dipeptidyl peptidase IV inhibitors and the like.

The sulfonylurea agents include acetohexamide, glibenclamide,gliclazide, glyclopyramide, chlorpropamide, tolazamide, tolbutamide,glimepiride and the like.

The biguanide preparations include buformin hydrochloride, metforminhydrochloride and the like.

The alfa-glucosidase inhibitors include acarbose, voglibose and thelike.

The fast-acting insulin secretion accelerators include nateglinide,repaglinide and the like.

The PPAR agonists include pioglitazone, troglitazone, rosiglitazone,JTT-501 and the like.

The insulin sensitizers having no PPAR agonistic activity includeONO-5816, YM-440 and the like.

The beta-3 adrenaline receptor activators include AJ9677, L750355,CP331648 and the like.

The aldose reductase inhibitors include epalrestat, fidarestat,zenarestat and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on cancer (malignant tumor) or cancer metastasis includeanticancer agents (MMP inhibitors, alkylating agents (cyclophosphamide,melphalan, thiotepa, mitomycin C, busulfan, procarbazine hydrochlorideand the like), metabolism antagonists (methotrexate, mercaptopurine,azathiopurine, fluorouracil, tegafur, cytarabine, azaserine and thelike), antibiotics (mitomycin C, bleomycin, peplomycin, doxorubicinhydrochloride, aclarubicin, daunorubicin, actinomycin C), antimitoticagents, platinum complex (cisplatin), plant-derived antimalignant tumoragents (vincristine sulfate, vinblastin sulfate and the like), antitumorhormones (methyltestosterone, testosterone propionate, testosteroneenanthate, mepitiostane, fosfestrol, chlormadinone acetate and thelike), immunoactivators (picibanil, krestin and the like), interferons(IFNα, IFNα-2a, IFNα-2b, IFNβ, IFNγ-1a and the like) and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on immunological diseases (autoimmune diseases, transplantationorgan rejections and the like) include immunosuppressants (ciclosporin,tacrolimus, FTY720 and the like).

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on dementia such as Alzheimer senile dementia includeacetylcholine esterase inhibitors, nicotine receptor regulating agents,cerebral circulation and metabolism improving agents, monoamine oxidaseinhibitors, vitamin E, aldose reductase inhibitors and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on epilepsy include phenyloin, trimetadione, ethosuximide,carbamazepine, phenobarbital, primidone, acetazolamide, sultiame, sodiumvalproate, clonazepam, diazepam, nitrazepam and the like.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) on arteriosclorosis include HMG-CoA reductase inhibitors,fibrate preparations, probucol preparations, anion-exchange resin, EPApreparations, nicotinic acid preparations, MTP inhibitors, otherantihypercholesterolemic agents, EDG-2 antagonists and the like.

Other drugs for supplementation and/or enhancement of the effect of thecompound represented by formulae (I) and (II) when employed inregenerative medicines include cytokines, various growth factors, suchas various CSF (G-CSF, GM-CSF and the like), various interleukins(IL-3,6,7,11, 12 and the like), EPO, TPO, SCF, FLT3 ligand, MIP-1α andthe like.

The weight proportion of the compound represented by formulae (I) and(II) and the other pharmaceutical preparations is not specificallylimited.

Arbitrary two or more of the other pharmaceutical preparations may beadministered in combination.

Other drugs for supplementation and/or enhancement of the prophylacticand/or therapeutic effect of the compound represented by formulae (I)and (II) include not only those which have so far been found but alsothose which will be found on the basis of the aforementioned mechanism.

In order to use the compound of the present invention represented byformulae (I) and (II) or the compound represented by formulae (I) and(II) in combination with the other pharmaceutical preparations, thesecompounds are normally administered to the entire or local part of humanbody orally or parenterally. It is preferable to select the mosteffective administration route upon treatment.

The doses to be administered are determined depending upon, for example,age, body weight, symptom, the desired therapeutic effect, the route ofadministration, and the duration of the treatment. In the human adult,the doses per person are generally from 1 ng to 100 mg, by oraladministration, up to several times per day, and from 0.1 ng to 10 mg,by parenteral administration, up to several times per day, or continuousadministration from 1 to 24 hours per day from vein.

As mentioned above, the doses to be used depend upon various conditions.Therefore, there are cases in which doses lower than or greater than theranges specified above may be used.

The compound represented by formulae (I) and (II) of the presentinvention, or concomitant drug combined the compound represented byformulae (I) and (II) with other drugs may be administered in thecomposition of, for example, solid compositions or liquid compositions,each for oral administration, or injections, external use,suppositories, each for parenteral administration.

Solid compositions for oral administration include compressed tablets,pills, capsules, dispersible powders and granules. Capsules include hardcapsules and soft capsules.

In such solid forms, one or more of the active compound(s) may beadmixed with vehicles (such as lactose, mannitol, glucose,microcrystalline cellulose, starch), binders (such as hydroxypropylcellulose, polyvinylpyrrolidone or magnesium metasilicate aluminate),disintegrants (such as cellulose calcium glycolate), lubricants (such asmagnesium stearate), stabilizing agents, and solution adjuvants (such asglutamic acid or aspartic acid) and prepared according to methods wellknown in normal pharmaceutical practice. The solid forms may, ifdesired, be coated with coating agents (such as sugar, gelatin,hydroxypropyl cellulose or hydroxypropylmethyl cellulose phthalate), orbe coated with two or more films. And further, coating may includecontainment within capsules of absorbable materials such as gelatin.

Liquid forms for oral administration include pharmaceutically acceptablesolutions, suspensions and emulsions, syrups and elixirs. In such forms,one or more of the active compound(s) may be dissolved, suspended oremulized into diluent(s) commonly used in the art (such as purifiedwater, ethanol or a mixture thereof). Besides such liquid forms may alsocomprise some additives, such as wetting agents, suspending agents,emulsifying agents, sweetening agents, flavoring agents, aroma,preservative or buffering agent.

Injections for parenteral administration include sterile aqueous,suspensions, emulsions and solid forms which are dissolved or suspendedinto solvent(s) for injection immediately before use. In injections, oneor more of the active compound(s) may be dissolved, suspended oremulized into solvent(s). The solvents may include distilled water forinjection, physiological salt solution, vegetable oil, propylene glycol,polyethylene glycol, alcohol, e.g. ethanol, or a mixture thereof.Injections may comprise some additives, such as stabilizing agents,solution adjuvants (such as glutamic acid, aspartic acid orPOLYSORBATE80 (registered trade mark)), suspending agents, emulsifyingagents, soothing agent, buffering agents, preservative. They may besterilized at a final step, or may be prepared by an asepticmanipulation. They may also be manufactured in the form of sterile solidforms, for example, freeze-dried products, which may be dissolved insterile water or some other sterile diluent(s) for injection immediatelybefore use.

In the parenteral administration, formulation of external use include,for example, ointment, ger, cream, poultice, patch, liniment, atomizedagent, inhalation, spray, aerosol, eye drops and nasal drops, etc. Theyincludes one or more of the active compound(s) and be prepared by knownmethod or usual method.

Ointment is prepared by known method or usual method. For example, it isprepared by levigation or fusion of one or more of the activecompound(s) and substrate. The substrate of ointment is selected fromknown or usual one. For example, higher fatty acid or higher fatty acidester (adipic acid, myristic acid, palmitic acid, stearic acid, oleicacid, adipic acid ester, myristic acid ester, palmitic acid ester,stearic acid ester, oleic acid ester, etc.), wax (yellow beeswax,Spermaceti, ceresin, etc.), surfactant (polyoxyethylene alkyl etherphosphoric acid ester, etc.), higher alcohol (cetanol, stearil alcohol,cetostearyl alcohol, etc.), silicon oil (dimethyl polysiloxane, etc.),hydrocarbon (hydrophilic petrolatum, white petrolatum, purified lanolin,light liquid paraffin, etc.), glycol (ethylene glycol, diethyleneglycol, propylene glycol, polyethylene glycol, macrogol, etc.),vegetable oil (castor oil, olive oil, sesame oil, turpentine oil, etc.),animal oil (mink oil, egg yolk oil, squalane, squalene, etc.), water,absorption accelerator, skin fit inhibitor, etc. are used as singlesubstance selected from them or mixture which consists of two or morekinds that is selected from them. Moreover, humectant, preservativeagent, stabilizer, antioxidative agent, fragrant materials, etc. may becontained.

Ger is prepared by known method or usual method. For example, it isprepared by fusion of one or more of the active compound(s) andsubstrate. The substrate of gel is selected from known or usual one. Forexample, lower alcohol (ethanol, isopropylalcohol, etc.), gelling agent(carboxy methyl cellulose, hydroxy ethyl cellulose, hydroxy propylcellulose, ethyl cellulose, etc.), neutralizing agent, (triethanolamine,diisopropanolamine, etc.), surfactant, (polyethylene glycolmonostearate, etc.), gum, water, absorption accelerator, skin fitinhibitor, etc. are used as single substance selected from them ormixture which consists of two or more kinds that is selected from them.Moreover, preservative agent, antioxidative agent, fragrant materials,etc. may be contained.

Cream is prepared by known method or usual method. For example, it isprepared by fusion or emulsification of one or more of the activecompound(s) and substrate. The substrate of cream is selected from knownor usual one. For example, higher fatty acid ester, lower alcohol,hydrocarbon, polyalcohol (propylene glycol, 1,3-butylene glycol, etc.),higher alcohol (2-hexyldecanol, cetanol, etc.), emulsifying agent(polyoxyethylene alkyl ether, fatty acid ester, etc.), water, absorptionaccelerator, skin fit inhibitor, etc. are used as single substanceselected from them or mixture which consists of two or more kinds thatis selected from them. Moreover, preservative agent, antioxidativeagent, fragrant materials, etc. may be contained.

Poultice is prepared by known method or usual method. For example, it isprepared by fusion of one or more of the active compound(s) andsubstrate, and then the kneaded one is laid over support medium. Thesubstrate for poultice is selected from known or usual one. For example,thickening agent (polyacrylic acid, polyvinylpyrolidone, gum acacia,starch, gelatin, methyl cellulose, etc.), bulking agent (kaolin, zincoxide, talc, calcium, magnesium, etc.), water, solubilizing agent,thickener, skin fit inhibitor, etc. are used as single substanceselected from them or mixture which consists of two or more kinds thatis selected from them. Moreover, preservative agent, antioxidativeagent, fragrant materials, etc. may be contained.

Patch is prepared by known method or usual method. For example, it isprepared by fusion of one or more of the active compound(s) andsubstrate, and then laid over support medium. The substrate for patch isselected from known or usual one. For example, polymer substrate, fat,higher fatty acid, thickener, skin fit inhibitor, etc. are used assingle substance selected from them or mixture which consists of two ormore kinds that is selected from them. Moreover, preservative agent,antioxidative agent, fragrant materials, etc. may be contained.

Liniment is prepared by known method or usual method. For example, oneor more of the active compound(s) may be dissolved, suspended oremulsified in water, alcohol (ethanol, polyethylene glycol, etc.),higher fatty acid, glycerin, soap, emulsifying agent, suspending agent,etc. as single substance selected from them or mixture which consists oftwo or more kinds that is selected from them. Moreover, preservativeagent, antioxidative agent, fragrant materials, etc. may be contained.

Atomized agent, inhalation and spray may comprise in addition to adiluent, a stabilizer such as sodium bisulfite and an isotonizationbuffer such as sodium chloride, sodium citrate or citric acid. Thepreparation process of sprays is described in detail in, for example,U.S. Pat. Nos. 2,868,691 and 3,095,355.

In case of administration of nasal drops, they may be usually sprayedintranasally in the form of liquid or powder comprising drugs with aspecial apparatus for nasal drops or nebulizer quantitatively.

The eye drops for parenteral administration may be in the form ofliquid, suspension, emulsion or ointment or may be dissolved in asolvent in use.

These eye drops are prepared by any known method. For example, one ormore active materials are dissolved, suspended or emulsified in asolvent. As such a solvent for eye drops there may be used sterilizedpurified water, physiological saline and other aqueous or nonaqueoussolvents (e.g., vegetable oil), singly or in combination. The eye dropsmay comprise an isotonic agent (e.g., sodium chloride, concentratedglycerin), a buffering agent (e.g., sodium phosphate, sodium acetate), asurface active agent (e.g., Polysolvate 80 (trade name), polyoxylstearate 40, polyoxyethylene-hardened castor oil), a stabilizer (sodiumcitrate, sodium edetate), a preservative (e.g., benzalconium chloride,Paraben), etc. properly selectively as necessary. The eye drops aresterilized at the final step or prepared by an aseptic manipulation.Alternatively, an aseptic solid agent such as freeze-dried product whichhas previously been prepared may be rendered aseptic or dissolved in anaseptic distilled water for injection or other solvent before use.

The dosage of inhalations for parenreral administration include aerosol,powders for inhalation or liquids for inhalation. The liquids forinhalation may be dissolved or suspended in water or the otherappropriate solvent as needed.

Such inhalations are prepared in a known method.

For example, a liquid for inhalation is prepared by selecting properadditives from an antiseptic (such as benzalkonium chloride orp-aminobenzonic acid), a coloring agent, a buffering agent (such assodium phosphate or sodium acetate), an isotonizing agent (such assodium chloride or concentrated glycerin), thickening agent (such ascarboxyvinylpolymer), or an accelerator of absorption, etc., ifnecessary.

A powder for inhalation is prepared by selecting proper additives from alubricant agent (such as stearin acid and the salt thereof), a bindingagent, (such as starch, dextrin), a diluting agent (such as lactose,cellulose), a coloring agent, an antiseptic (such as benzalkoniumchloride or p-aminobenzonic acid), an accelerator of absorption, etc.,if necessary.

In case of administration of liquid for inhalation, spray (atomizer,nebulizer) is usually used and in case of administration of powder forinhalation, inhalation administration apparatus for powder agents isusually used.

The other compositions for parenteral administration includesuppositories for intrarectal administration and pessaries for vaginaladministration which comprise one or more of the active substance(s) andmay be prepared by methods known per se.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention is explained below in detail based on ReferenceExamples and Examples, but the present invention is not limited thereto.

All the compounds described in the present specification were namedaccording to IUPAC nomenclature system or named using ACD/Name (ver.6.0, Advanced Chemistry Development Inc.)

The solvents in the parentheses show the developing solvents or elutingsolvents and the ratios of the solvents used are by volume inchromatographic separations or TLC. The solvents in the parentheses inNMR show the solvents for measurement. Electrospray ionization (ESI,condition: Pos., 20 V) was used as a method of Mass measurement.

HPLC condition is outlined below.

(1) Condition A (Analysis)

Used equipment: Waters LC/MS

Column: Xterra (registered trade name) MS C₁₈, 5 μm, 4.6×50 mm I.D.

Flow rate: 3 mL/min

Solvent: Liquid A: 0.1% trifluoroacetic acid aqueous solution

Liquid B: 0.1% trifluoroacetic acid-acetonitrile solution

Time (min.) liquid A Liquid B 0 95 5 0.5 95 5 3 0 100 3.5 0 100 3.51 955 5 95 5

(2) Condition B (Analysis)

Used equipment: Waters LC/MS

Column: Xterra (registered trade name) MS C₁₈, 5 μm, 4.6×50 mm I.D.

Flow rate: 3 mL/min

Solvent: Liquid A: 0.1% triethylamine aqueous solution

Liquid B: 0.1% triethylamine-acetonitrile solution

Time (min.) Liquid A Liquid B 0 95 5 0.5 95 5 3 0 100 3.5 0 100 3.51 955 7 95 5

Reference Example 1 2-chloro-4-(perhydroazepin-1-yl)pyrimidine

To a solution of 2,4-dichloropyrimidine (3.0 g) in tetrahydrofuran (50mL) were added triethylamine (4.2 mL) and perhydroazepine (2.5 mL) withice cooling and the mixture was stirred for 1 hour at room temperature.To the reaction mixture was added water (30 mL) and the resultingmixture was concentrated. The residue was extracted with methylenechloride three times. The organic layer was washed with brine, driedover anhydrous magnesium sulfate and concentrated. The residue waspurified by column chromatography on silica gel (hexane:ethylacetate=5:1→2:1) to give the title compound (3.03 g) having thefollowing physical data.

TLC: Rf 0.18 (hexane:ethyl acetate=3:1);

NMR (CDCl₃): δ 1.53 (m, 4H), 1.78 (m, 4H), 3.44 (m, 2H), 3.83 (m, 2H),6.29 (d, J=6.32 Hz, 1H), 7.96 (d, J=6.32 Hz, 1H).

Example 12-(2-dimethylaminoethylamino)-4-(perhydroazepin-1-yl)pyrimidine

A mixture of the compound prepared in Reference Example 1 (1.5 g) andN,N-dimethylethylenediamine (1.56 mL) was stirred for 16 hour at 90° C.The reaction mixture was cooled and purified by column chromatography onsilica gel (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.2) togive the title compound (1.44 g) having the following physical data.

crystalline powder: melting point 53.0-54.5° C.;

TLC: Rf 0.30 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆, 363.1K): δ 1.50 (m, 4H), 1.70 (m, 4H), 2.19 (s, 6H), 2.42(t, J=6.00 Hz, 2H), 3.33 (q, J=6.00 Hz, 2H), 3.56 (m, 4H), 5.74 (m, 1H),5.83 (d, J=6.00 Hz, 1H), 7.72 (d, J=6.00 Hz, 1H).

Example 1(1) to Example 1(47)

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 1(1)2-[3-(imidazol-1-yl)propylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.66 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.49 (m, 4H), 1.69 (m, 4H), 1.97 (m, 2H), 3.24 (m, 2H),3.54 (m, 4H), 4.01 (t, J=7.00 Hz, 2H), 5.84 (d, J=6.04 Hz, 1H), 6.12 (m,1H), 6.86 (d, J=1.24 Hz, 1H), 7.10 (d, J=1.24 Hz, 1H), 7.56 (s, 1H),7.73 (d, J=6.04 Hz, 1H).

Example 1(2)2-(2-dimethylaminopropylamino)-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.57 (chloroform:methanol: 28% ammonia water=80:10:1);

NMR (DMSO-d₆, 363.1K): δ 0.91 (d, J=6.59 Hz, 3H), 1.50 (m, 4H), 1.69 (m,4H), 2.20 (s, 6H), 2.72 (m, 1H), 3.20 (m, 2H), 3.55 (t, J=6.00 Hz, 4H),5.67 (m, 1H), 5.83 (d, J=5.77 Hz, 1H), 7.72 (d, J=5.77 Hz, 1H).

Example 1(3) 4-(2-dimethylaminoethylamino)-2-pyrrolidinopyrimidine

TLC: Rf 0.29 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.84 (m, 4H), 2.17 (s, 6H), 2.38 (t, J=6.73 Hz, 2H),3.37 (m, 6H), 5.70 (d, J=5.50 Hz, 1H), 6.77 (m, 1H), 7.64 (d, J=5.50 Hz,1H).

Example 1(4)4-(2-dimethylaminoethylamino)-2-(perhydroazocin-1-yl)pyrimidine

TLC: Rf 0.38 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.43 (m, 6H), 1.69 (m, 4H), 2.15 (s, 6H), 2.36 (t,J=6.73 Hz, 2H), 3.32 (m, 2H), 3.58 (m, 4H), 5.68 (d, J=5.50 Hz, 1H),6.77 (m, 1H), 7.65 (d, J=5.50 Hz, 1H).

Example 1(5) 4-(2-dimethylaminoethylamino)-2-piperidinopyrimidine

TLC: Rf 0.44 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.44 (m, 4H), 1.56 (m, 2H), 2.15 (s, 6H), 2.35 (t,J=6.00 Hz, 2H), 3.33 (m, 2H), 3.63 (t, J=6.00 Hz, 4H), 5.70 (d, J=5.77Hz, 1H), 6.76 (s, 1H), 7.66 (d, J=5.77 Hz, 1H).

Example 1(6)2-(2-dimethylamino-1-methylethylamino)-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.52 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CD₃OD): δ 1.18 (d, J=6.32 Hz, 3H), 1.55 (m, 4H), 1.76 (m, 4H), 2.28(m, 7H), 2.51 (m, 1H), 3.58 (m, 4H), 4.15 (m, 1H), 5.90 (d, J=6.04 Hz,1H), 7.67 (d, J=6.04 Hz, 1H).

Example 1(7)4-(2-dimethylaminoethylamino)-2-(4-methylpiperazin-1-yl)pyrimidine

NMR (DMSO-d₆): δ 2.20 (s, 3H), 2.26 (s, 6H), 2.32 (m, 4H), 3.30 (m, 4H),3.63 (m, 4H), 5.76 (d, J=5.20 Hz, 1H), 6.91 (m, 1H), 7.69 (d, J=5.20 Hz,1H);

MS (m/z): 265 (M+H)⁺;

HPLC retention time (min): 2.83; HPLC condition: B.

Example 1(8)4-(2-dimethylaminoethylamino)-2-(4-phenylpiperazin-1-yl)pyrimidine

MS (m/z): 327 (M+H)⁺;

HPLC retention time (min): 3.51; HPLC condition: B.

Example 1(9)2-(4-benzylpiperazin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 341 (M+H)⁺;

HPLC retention time (min): 3.42; HPLC condition: B.

Example 1(10)2-(4-acetylpiperazin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 293 (M+H)⁺;

HPLC retention time (min): 2.78; HPLC condition: B.

Example 1(11)4-(2-dimethylaminoethylamino)-2-(4-hydroxypiperidin-1-yl)pyrimidine

MS (m/z): 266 (M+H)⁺;

HPLC retention time (min): 2.76; HPLC condition: B.

Example 1(12)4-(2-dimethylaminoethylamino)-2-(4-methylpiperidin-1-yl)pyrimidine

MS (m/z): 264 (M+H)⁺;

HPLC retention time (min): 3.49; HPLC condition: B.

Example 1(13)4-(2-dimethylaminoethylamino)-2-(3-methylpiperidin-1-yl)pyrimidine

MS (m/z): 264 (M+H)⁺;

HPLC retention time (min): 3.46; HPLC condition: B.

Example 1(14)4-(2-dimethylaminoethylamino)-2-(2-methylpiperidin-1-yl)pyrimidine

MS (m/z): 264 (M+H)⁺;

HPLC retention time (min): 2.89; HPLC condition: B.

Example 1(15)2-(3-hydroxypyrrolidin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 252 (M+H)⁺;

HPLC retention time (min): 2.70; HPLC condition: B.

Example 1(16)2-(4-ethoxycarbonylpiperidin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 322 (M+H)⁺;

HPLC retention time (min): 3.31; HPLC condition: B.

Example 1(17)2-(3-ethoxycarbonylpiperidin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 322 (M+H)⁺;

HPLC retention time (min): 3.33; HPLC condition: B.

Example 1(18) 2-thiomorpholino-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 268 (M+H)⁺;

HPLC retention time (min): 3.18; HPLC condition: B.

Example 1(19) 4-(2-dimethylaminoethylamino)-2-morpholinopyrimidine

MS (m/z): 252 (M+H)⁺;

HPLC retention time (min): 2.83; HPLC condition: B.

Example 1(20)2-(4-carbamoylpiperidin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 585 (2M+H)⁺, 293 (M+H)⁺;

HPLC retention time (min): 2.72; HPLC condition: B.

Example 1(21)2-(3-carbamoylpiperidin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 293 (M+H)⁺;

HPLC retention time (min): 2.78; HPLC condition: B.

Example 1(22)2-(4-benzyloxycarbonyl-1,4-perhydrodiazepin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 797 (2M+H)⁺, 399 (M+H)⁺;

HPLC retention time (min): 3.44; HPLC condition: B.

Example 1(23)2-(4-benzyl-1,4-perhydrodiazepin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 355 (M+H)⁺;

HPLC retention time (min): 3.47; HPLC condition: B.

Example 1(24)4-(2-dimethylaminoethylamino)-2-(perhydroquinolin-1-yl)pyrimidine

MS (m/z): 304 (M+H)⁺;

HPLC retention time (min): 3.84; HPLC condition: B.

Example 1(25)4-(2-dimethylaminoethylamino)-2-(perhydroisoquinolin-2-yl)pyrimidine

MS (m/z): 304 (M+H)⁺;

HPLC retention time (min): 3.86; HPLC condition: B.

Example 1(26)4-(2-dimethylaminoethylamino)-2-(4-methyl-1,4-perhydrodiazepin-1-yl)pyrimidine

MS (m/z): 279 (M+H)⁺;

HPLC retention time (min): 2.90; HPLC condition: B.

Example 1(27)4-(2-dimethylaminoethylamino)-2-(4-propylpiperidin-1-yl)pyrimidine

MS (m/z): 292 (M+H)⁺;

HPLC retention time (min): 3.89; HPLC condition: B.

Example 1(28)2-(4-butylpiperazin-1-yl)-4-(2-dimethylaminoethylamino)pyrimidine

MS (m/z): 307 (M+H)⁺;

HPLC retention time (min): 3.34; HPLC condition: B.

Example 1(29)4-(2-dimethylaminoethylamino)-2-(1,2,3,6-tetrahydropyridin-1-yl)pyrimidine

MS (m/z): 248 (M+H)⁺;

HPLC retention time (min): 3.25; HPLC condition: B.

Example 1(30)4-(2-dimethylaminoethylamino)-2-(3,5-dimethylpiperidin-1-yl)pyrimidine

MS (m/z): 278 (M+H)⁺;

HPLC retention time (min): 3.67; HPLC condition: B.

Example 1(31)4-(2-dimethylaminoethylamino)-2-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.41 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 7.65 (brd, J=5.7 Hz, 1H), 6.72 (br, 1H), 5.68 (d, J=5.7Hz, 1H), 3.61 (m, 4H), 3.30 (m, 2H), 2.36 (t, J=6.9 Hz, 2H), 2.15 (s,6H), 1.65 (m, 4H), 1.44 (m, 4H).

Example 1(32) 2-(3-dimethylaminopropylamino)-4-pyrrolidinopyrimidine

TLC: Rf 0.19 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.60 (m, 2H), 1.87 (m, 4H), 2.10 (s, 6H), 2.22 (t,J=7.14 Hz, 2H), 3.20 (m, 2H), 3.38 (m, 4H), 5.66 (d, J=5.77 Hz, 1H),6.37 (m, 1H), 7.70 (d, J=5.77 Hz, 1H).

Example 1(33) 2-(3-dimethylaminopropylamino)-4-piperidinopyrimidine

TLC: Rf 0.28 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.46 (m, 4H), 1.60 (m, 4H), 2.11 (s, 6H), 2.22 (t,J=7.14 Hz, 2H), 3.18 (m, 2H), 3.49 (m, 4H), 5.95 (d, J=6.04 Hz, 1H),6.41 (m, 1H), 7.72 (d, J=6.04 Hz, 1H).

Example 1(34)2-(3-dimethylaminopropylamino)-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.19 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.44 (m, 4H), 1.61 (m, 6H), 2.09 (s, 6H), 2.21 (t,J=7.14 Hz, 2H), 3.18 (q, J=6.59 Hz, 2H), 3.51 (m, 4H), 5.81 (d, J=6.04Hz, 1H), 6.41 (m, 1H), 7.70 (d, J=6.04 Hz, 1H).

Example 1(35) 2-(2-dimethylaminoethylamino)-4-pyrrolidinopyrimidine

TLC: Rf 0.20 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.87 (m, 4H), 2.15 (s, 6H), 2.36 (t, J=6.73 Hz, 2H),3.35 (m, 6H), 5.68 (d, J=5.77 Hz, 1H), 6.14 (m, 1H), 7.71 (d, J=5.77 Hz,1H).

Example 1(36)2-(2-dimethylaminoethylamino)-6-methyl-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.30 (chloroform:methanol: triethylamine=80:10:1);

NMR (DMSO-d₆): δ 1.45 (m, 4H), 1.67 (m, 4H), 2.05 (s, 3H), 2.19 (s, 6H),2.41 (t, J=6.90 Hz, 2H), 3.29 (m, 2H), 3.65 (m, 4H), 5.73 (s, 1H), 6.15(m, 1H).

Example 1(37)2-(2-dimethylaminoethylamino)-5-methyl-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.32 (chloroform:methanol: triethylamine=80:10:1);

NMR (DMSO-d₆): δ 1.47 (m, 4H), 1.69 (m, 4H), 2.08 (s, 3H), 2.14 (s, 6H),2.34 (t, J=6.60 Hz, 2H), 3.25 (td, J=6.60, 6.00 Hz, 2H), 3.60 (t, J=6.00Hz, 4H), 6.00 (m, 1H), 7.52 (s, 1H).

Example 1(38)2-(1-benzylpiperidin-4-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.52 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆, 363.1K): δ 1.49 (m, 6H), 1.68 (m, 4H), 1.87 (m, 2H), 2.07(td, J=11.47, 2.61 Hz, 2H), 2.77 (m, 2H), 3.46 (s, 2H), 3.54 (t, J=6.00Hz, 4H), 3.66 (m, 1H), 5.74 (m, 1H), 5.82 (d, J=6.04 Hz, 1H), 7.25 (m,5H), 7.72 (d, J=6.04 Hz, 1H).

Example 1(39)2-(2-morpholinoethylamino)-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.41 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.45 (m, 4H), 1.68 (m, 4H), 2.38 (m, 6H), 3.30 (q,J=6.00 Hz, 2H), 3.57 (m, 8H), 5.83 (d, J=5.70 Hz, 1H), 6.19 (m, 1H),7.71 (d, J=5.70 Hz, 1H).

Example 1(40)4-(perhydroazepin-1-yl)-2-(2-pyrrolidinoethylamino)pyrimidine

TLC: Rf 0.23 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆, 363.1K): δ 1.51 (m, 4H), 1.74 (m, 8H), 2.69 (m, 4H), 2.75(t, J=6.60 Hz, 2H), 3.42 (m, 2H), 3.56 (m, 4H), 5.86 (d, J=6.00 Hz, 1H),5.99 (m, 1H), 7.73 (d, J=6.00 Hz, 1H).

Example 1(41) 2-(2-aminoethylamino)-4-(perhydroazepin-1-yl)pyrimidinedihydro chloride

crystalline powder: melting point 100-102° C.;

TLC: Rf 0.16 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CD₃OD): δ 1.61 (m, 4H), 1.85 (m, 4H), 3.22 (t, J=6.00 Hz, 2H), 3.70(m, 2H), 3.75 (t, J=6.00 Hz, 2H), 3.93 (m, 2H), 6.44 (d, J=7.70 Hz, 1H),7.72 (d, J=7.70 Hz, 1H).

Example 1(42)(±)-2-[(1R*,2R*)-2-aminocyclohexylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.23 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.11 (m, 4H), 1.45 (m, 4H), 1.62 (m, 6H), 1.81 (m, 1H),1.97 (m, 1H), 3.37 (m, 6H), 5.82 (d, J=5.80 Hz, 1H), 6.19 (m, 1H), 7.70(d, J=5.80 Hz, 1H).

Example 1(43)(±)-2-[(1S*,2R*)-2-aminocyclohexylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.19 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.25 (m, 2H), 1.47 (m, 10H), 1.68 (m, 4H), 2.96 (m,1H), 3.37 (m, 4H), 3.73 (m, 1H), 5.83 (d, J=5.80 Hz, 1H), 5.91 (m, 1H),7.71 (d, J=5.80 Hz, 1H).

Example 1(44)2-(2-dimethylaminoethylamino)-4-(perhydroquinolin-1-yl)pyrimidine

TLC: Rf 0.50 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆, 373.1K): δ 1.37 (m, 6H), 1.60 (m, 2H), 1.80 (m, 5H), 2.62(s, 6H), 2.84 (m, 1H), 2.98 (m, 2H), 3.54 (m, 2H), 4.16 (m, 1H), 4.36(m, 1H), 6.08 (d, J=6.32 Hz, 1H), 6.74 (m, 1H), 7.77 (d, J=6.32 Hz, 1H).

Example 1(45)4-(4-acetylpiperazin-1-yl)-2-(2-dimethylaminoethylamino)pyrimidine

TLC: Rf 0.40 (chloroform:methanol:28% ammonia water=80:10:1)

NMR (DMSO-d₆): δ 2.02 (s, 3H), 2.54 (s, 6H), 2.87 (t, J=6.32 Hz, 2H),3.40 (m, 10H), 6.09 (d, J=6.04 Hz, 1H), 6.64 (m, 1H), 7.83 (d, J=6.04Hz, 1H).

Example 1(46)2-(2-dimethylaminoethylamino)-4-(3-methylpiperidin-1-yl)pyrimidine

TLC: Rf 0.50 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 0.86 (d, J=6.60 Hz, 3H), 1.14 (m, 1H), 1.34 (m, 1H),1.48 (m, 1H), 1.62 (m, 1H), 1.78 (m, 1H), 2.14 (s, 6H), 2.34 (t, J=6.90Hz, 2H), 2.44 (m, 1H), 2.76 (m, 1H), 3.27 (m, 2H), 4.16 (m, 2H), 5.98(d, J=5.80 Hz, 1H), 6.20 (m, 1H), 7.73 (d, J=5.80 Hz, 1H).

Example 1(47)2-(2-aminoethylamino)-5-bromo-4-(perhydroazepin-1-yl)pyrimidinedihydrochloride

TLC: Rf 0.60 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CD₃OD): δ 1.65 (m, 4H), 1.90 (m, 4H), 3.21 (t, J=6.00 Hz, 2H), 3.73(t, J=6.00 Hz, 2H), 4.11 (m, 4H), 8.06 (s, 1H).

Reference Example 2 2-chloro-4-(perhydroazepin-1-yl)quinazoline

To a solution of 2,4-dichloroquinazoline (1.0 g) in tetrahydrofuran (10mL) were added triethylamine (2.1 mL) and perhydroazepine (0.745 mL)with ice cooling and the mixture was stirred for 1 hour at roomtemperature. To the reaction mixture was added water (20 mL) and theresulting mixture was concentrated. The residue was extracted withmethylene chloride three times. The organic layer was washed with brine,dried over anhydrous magnesium sulfate and concentrated. The residue waswashed with hexane-diethyl ether (10:1) to give the title compound (991mg) having the following physical data.

TLC: Rf 0.31 (hexane:ethyl acetate=3:1); MS (m/z): 264, 262 (M+H)⁺;

HPLC retention time (min) 3.34; HPLC condition: A.

Example 2 2-(2-diethylaminoethylamino)-4-(perhydroazepin-1-yl)quinazoline

To a solution of the compound prepared in Reference Example 2 (300 mg)in 2-propanol (3 mL) was added N,N-diethylethylenediamine (0.49 m) andthe mixture was stirred for 16 hours at 80° C. The reaction mixture wascooled and the residue was purified by column chromatography on silicagel (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.3) to give thecompound (267 mg) of the present invention having the following physicaldata.

TLC: Rf 0.43 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CDCl₃): δ 7.80 (d, J=7.5 Hz, 1H), 7.45 (m, 2H), 6.98 (m, 1H), 5.26(br, 1H), 3.87 (m, 4H), 3.53 (m, 2H), 2.66 (t, J=6.3 Hz, 2H), 2.58 (q,J=6.9 Hz, 4H), 1.97 (m, 4H), 1.66 (m, 4H), 1.04 (t, J=6.9 Hz, 6H); MS(m/z): 342 (M+H)⁺, 171;

HPLC retention time (min): 2.96 min.; HPLC condition: A.

Example 2(1) to Example 2(95)

By the same procedure as described in Reference Example 2→Example 2using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 2(1)2-[2-[N,N-bis(2-hydroxyethyl)amino]ethylamino]-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.78; MS (m/z): 346 (M+H)⁺, 242; HPLCcondition: A.

Example 2(2) 2-[3-(imidazol-1-yl)propylamino]-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.96; MS (m/z): 323 (M+H)⁺, 215; HPLCcondition: A.

Example 2(3) 2-(2-morpholinoethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.77; MS (m/z): 328 (M+H)⁺, 242; HPLCcondition: A.

Example 2(4)2-[3-(2-methylpiperidin-1-yl)propylamino]-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.98; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(5)2-[2-[N,N-bis(2-hydroxyethyl)amino]ethylamino]-4-piperidinoquinazoline

HPLC retention time (min): 2.87; MS (m/z): 719(2M+H)⁺, 360 (M+H)⁺; HPLCcondition: A.

Example 2(6) 2-[3-(imidazol-1-yl)propylamino]-4-piperidinoquinazoline

HPLC retention time (min): 3.01; MS (m/z): 337 (M+H)⁺, 229; HPLCcondition: A.

Example 2(7) 2-(2-morpholinoethylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.90; MS (m/z): 342 (M+H)⁺; HPLC condition:A.

Example 2(8) 2-(3-pyrrolidinopropylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.98; MS (m/z): 340 (M+H)⁺, 229; HPLCcondition: A.

Example 2(9)2-[2-(1-methylpyrrolidin-2-yl)ethylamino]-4-piperidinoquinazoline

HPLC retention time (min): 2.98; MS (m/z): 340 (M+H)⁺, 170.5; HPLCcondition: A.

Example 2(10)2-(1-ethylpyrrolidin-2-ylmethylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.96; MS (m/z): 340 (M+H)⁺; HPLC condition:A.

Example 2(11)2-(2,2-dimethyl-3-dimethylaminopropylamino)-4-piperidinoquinazoline

HPLC retention time (min): 3.00; MS (m/z): 342 (M+H)⁺; HPLC condition:A.

Example 2(12) 2-(2-dimethylaminopropylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.94; MS (m/z): 314 (M+H)⁺; HPLC condition:A.

Example 2(13) 2-(2-diethylaminoethylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.94; MS (m/z): 328 (M+H)⁺; HPLC condition:A.

Example 2(14) 2-(3-diethylaminopropylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.98; MS (m/z): 342 (M+H)⁺, 314, 229; HPLCcondition: A.

Example 2(15) 2-(3-morpholinopropylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.96; MS (m/z): 356 (M+H)⁺, 178.5; HPLCcondition: A.

Example 2(16)2-[3-[N,N-bis(2-hydroxyethyl)amino]propylamino]-4-piperidinoquinazoline

HPLC retention time (min): 2.92; MS (m/z): 374 (M+H)⁺, 356, 314; HPLCcondition: A.

Example 2(17) 2-(3-dimethylaminopropylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.96; MS (m/z): 314 (M+H)⁺; HPLC condition:A.

Example 2(18)2-(2-dimethylamino-1-methylethylamino)-4-piperidinoquinazoline

HPLC retention time (min): 2.92; MS (m/z): 314 (M+H)⁺; HPLC condition:A.

Example 2(19)2-[3-(2-methylpiperidin-1-yl)propylamino]-4-piperidinoquinazoline

HPLC retention time (min): 3.03; MS (m/z): 368 (M+H)⁺, 229; HPLCcondition: A.

Example 2(20)2-[2-[N,N-bis(2-hydroxyethyl)amino]ethylamino]-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 2.90; MS (m/z): 747 (2M+H)⁺, 374 (M+H)⁺; HPLCcondition: A.

Example 2(21)2-[3-(imidazol-1-yl)propylamino]-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.09; MS (m/z): 351 (M+H)⁺; HPLC condition:A.

Example 2(22)2-(2-morpholinoethylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 2.96; MS (m/z): 711 (2M+H)⁺, 356 (M+H)⁺; HPLCcondition: A.

Example 2(23)2-(3-pyrrolidinopropylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.05; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(24)2-[2-(1-methylpyrrolidin-2-yl)ethylamino]-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.03; MS (m/z): 707 (2M+H)⁺, 354 (M+H)⁺; HPLCcondition: A.

Example 2(25)2-(1-ethylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.03; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(26)2-(2,2-dimethyl-3-dimethylaminopropylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.05; MS (m/z): 711 (2M+H)⁺, 356 (M+H)⁺; HPLCcondition: A.

Example 2(27)2-(2-dimethylaminopropylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.01; MS (m/z): 328 (M+H)⁺; HPLC condition:A.

Example 2(28)2-(3-diethylaminopropylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.05; MS (m/z): 356 (M+H)⁺; HPLC condition:A.

Example 2(29)2-(3-morpholinopropylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.00; MS (m/z): 370 (M+H)⁺; HPLC condition:A.

Example 2(30)2-[3-[N,N-bis(2-hydroxyethyl)amino]propylamino]-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 2.96; MS (m/z): 388(M+H)⁺; HPLC condition: A.

Example 2(31)2-(2-dimethylamino-1-methylethylamino)-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 2.98; MS (m/z): 328 (M+H)⁺; HPLC condition:A.

Example 2(32)2-[3-(2-methylpiperidin-1-yl)propylamino]-4-(perhydroazepin-1-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 382 (M+H)⁺, 243; HPLCcondition: A.

Example 2(33) 2-(2-dimethylaminoethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.83; MS (m/z): 286 (M+H)⁺, 241; HPLCcondition: A.

Example 2(34) 2-(2-pyrrolidinoethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 3.11; MS (m/z): 312 (M+H)⁺, 241; HPLCcondition: A.

Example 2(35) 2-(3-pyrrolidinopropylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.89; MS (m/z): 326 (M+H)⁺, 215; HPLCcondition: A.

Example 2(36) 2-(2-piperidinoethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.90; MS (m/z): 326 (M+H)⁺; HPLC condition:A.

Example 2(37)2-(2-(1-methylpyrrolidin-2-yl)ethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.90; MS (m/z): 651 (2M+H)⁺, 326 (M+H)⁺; HPLCcondition: A.

Example 2(38)2-(1-ethylpyrrolidin-2-ylmethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.89; MS (m/z): 326 (M+H)⁺; HPLC condition:A.

Example 2(39)2-(2,2-dimethyl-3-dimethylaminopropylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.94; MS (m/z): 328 (M+H)⁺; HPLC condition:A.

Example 2(40) 2-(2-dimethylaminopropylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.89; MS (m/z): 300 (M+H)⁺, 150.5; HPLCcondition: A.

Example 2(41) 2-(2-diethylaminoethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.89; MS (m/z): 314 (M+H)⁺, 241; HPLCcondition: A.

Example 2(42) 2-(3-diethylaminopropylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.92; MS (m/z): 328 (M+H)⁺; HPLC condition:A.

Example 2(43) 2-(3-morpholinopropylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.89; MS (m/z): 342 (M+H)⁺; HPLC condition:A.

Example 2(44)2-[3-[N,N-bis(2-hydroxyethyl)amino]propylamino]-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.89; MS (m/z): 360 (M+H)⁺; HPLC condition:A.

Example 2(45) 2-(3-dimethylaminopropylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.89; MS (m/z): 300 (M+H)⁺, 255; HPLCcondition: A.

Example 2(46)2-(2-dimethylamino-1-methylethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.87; MS (m/z): 300 (M+H)⁺; HPLC condition:A.

Example 2(47)2-(1-methylpyrrolidin-2-ylmethylamino)-4-pyrrolidinoquinazoline

HPLC retention time (min): 2.91; MS (m/z): 312 (M+H)⁺; HPLC condition:A.

Example 2(48)2-[2-[N,N-bis(2-hydroxyethyl)amino]ethylamino]-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.00; MS (m/z): 775 (2M+H)⁺, 388 (M+H)⁺; HPLCcondition: A.

Example 2(49)2-(2-pyrrolidinoethylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.02; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(50)2-(3-imidazol-1-ylpropylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.07; MS (m/z): 729 (2M+H)⁺, 365 (M+H)⁺; HPLCcondition: A.

Example 2(51)2-(2-morpholinoethylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.01; MS (m/z): 739 (2M+H)⁺, 370 (M+H)⁺; HPLCcondition: A.

Example 2(52)2-(3-pyrrolidinopropylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 368 (M+H)⁺, 184.5; HPLCcondition: A.

Example 2(53)2-(2-piperidinoethylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.07; MS (m/z): 368 (M+H)⁺, 184.5; HPLCcondition: A.

Example 2(54)2-[2-(1-methylpyrrolidin-2-yl)ethylamino]-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.09; MS (m/z): 735 (2M+H)⁺, 368 (M+H)⁺; HPLCcondition: A.

Example 2(55)2-(1-ethylpyrrolidin-2-ylmethylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.09; MS (m/z): 368 (M+H)⁺, 207; HPLCcondition: A.

Example 2(56)2-(3-dimethylamino-2,2-dimethylpropylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 370 (M+H)⁺; HPLC condition:A.

Example 2(57)2-(2-dimethylaminopropylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.07; MS (m/z): 342 (M+H)⁺; HPLC condition:A.

Example 2(58)2-(2-diethylaminoethylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.05; MS (m/z): 356 (M+H)⁺; HPLC condition:A.

Example 2(59)2-(3-diethylaminopropylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 370 (M+H)⁺, 185.5; HPLCcondition: A.

Example 2(60)2-(3-morpholinopropylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.07; MS (m/z): 384 (M+H)⁺; HPLC condition:A.

Example 2(61)2-[3-[N,N-bis(2-hydroxyethyl)amino]propylamino]-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.03; MS (m/z): 402 (M+H)⁺; HPLC condition:A.

Example 2(62)2-(3-dimethylaminopropylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.07; MS (m/z): 342 (M+H)⁺, 297; HPLCcondition: A.

Example 2(63)2-(2-dimethylamino-1-methylethylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.02; MS (m/z): 342 (M+H)⁺; HPLC condition:A.

Example 2(64)2-[3-(2-methylpiperidin-1-yl)propylamino]-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.14; MS (m/z): 396 (M+H)⁺, 198.5; HPLCcondition: A.

Example 2(65)2-(1-methylpyrrolidin-2-ylmethylamino)-4-(perhydroazocin-1-yl)quinazoline

HPLC retention time (min): 3.07; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(66)2-[2-[N,N-bis(2-hydroxyethyl)amino]ethylamino]-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.01; MS (m/z): 799 (2M+H)⁺, 400 (M+H)⁺; HPLCcondition: A.

Example 2(67)2-(2-pyrrolidinoethylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.09; MS (m/z): 366 (M+H)⁺, 207; HPLCcondition: A.

Example 2(68)2-[3-(imidazol-1-ylamino)propyl]-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 753 (2M+H)⁺, 377 (M+H)⁺; HPLCcondition: A.

Example 2(69)2-(2-morpholinoethylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.05; MS (m/z): 763(2M+H)⁺, 382 (M+H)⁺; HPLCcondition: A.

Example 2(70)2-(3-pyrrolidinopropylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 380 (M+H)⁺, 190.5; HPLCcondition: A.

Example 2(71)2-(2-piperidinoethylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 380 (M+H)⁺; HPLC condition:A.

Example 2(72)2-[2-(1-methylpyrrolidin-2-yl)ethylamino]-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 380 (M+H)⁺; HPLC condition:A.

Example 2(73)2-(1-ethylpyrrolidin-2-ylmethylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.11; MS (m/z): 380 (M+H)⁺; HPLC condition:A.

Example 2(74)2-[3-dimethylamino-2,2-dimethylpropylamino]-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.14; MS (m/z): 382 (M+H)⁺; HPLC condition:A.

Example 2(75)2-(2-dimethylaminopropylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.09; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(76)2-(2-diethylaminoethylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.06; MS (m/z): 368 (M+H)⁺; HPLC condition:A.

Example 2(77)2-(3-diethylaminopropylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.14; MS (m/z): 382 (M+H)⁺, 191.5; HPLCcondition: A.

Example 2(78)2-(3-morpholinopropylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.08; MS (m/z): 791 (2M+H)⁺, 396 (M+H)⁺; HPLCcondition: A.

Example 2(79)2-[3-[N,N-bis(2-hydroxyethyl)amino]propylamino]-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.05; MS (m/z): 414 (M+H)⁺; HPLC condition:A.

Example 2(80)2-(3-dimethylaminopropylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.09; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(81)2-(2-dimethylamino-1-methylethylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.07; MS (m/z): 354 (M+H)⁺; HPLC condition:A.

Example 2(82)2-[3-(2-methylpiperidin-1-yl)propylamino]-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.18; MS (m/z): 408 (M+H)⁺; HPLC condition:A.

Example 2(83)2-(1-methylpyrrolidin-2-ylmethylamino)-4-(3-azabicyclo[3.2.2]nonan-3-yl)quinazoline

HPLC retention time (min): 3.09; MS (m/z): 731 (2M+H)⁺, 366 (M+H)⁺; HPLCcondition: A.

Example 2(84) 2-(2-dimethylaminoethylamino)-4-piperidinoquinazoline

MS (m/z): 300 (M+H)⁺;

HPLC retention time (min): 3.83; HPLC condition: B.

Example 2(85) 2-(2-pyrrolidino ethylamino)-4-piperidinoquinazoline

NMR (DMSO-d₆): δ 7.66 (d, J=7.2 Hz, 1H), 7.48 (m, 1H), 7.30 (d, J=8.4Hz, 1H), 7.04 (t, J=7.2 Hz, 1H), 6.51 (m, 1H), 3.50 (m, 4H), 3.43 (m,2H), 3.25 (m, 2H), 3.15 (m, 2H), 2.57 (t, J=6.9 Hz, 2H), 1.66 (m, 10H);

MS (m/z): 326 (M+H)⁺, 283;

HPLC retention time (min): 4.16; HPLC condition: B.

Example 2(86) 2-(2-piperidinoethylamino)-4-piperidinoquinazoline

NMR (DMSO-d₆): δ 7.66 (dd, J=8.4, 0.9 Hz, 1H), 7.49 (m, 1H), 7.30 (d,J=8.1 Hz, 1H), 7.04 (t, J=7.2 Hz, 1H), 6.45 (m, 1H), 3.40 (m, 4H), 3.43(m, 2H), 2.45 (t, J=7.2 Hz, 2H), 2.37 (m, 4H), 1.66 (m, 6H), 1.49 (m,4H), 1.38 (m, 2H);

MS (m/z): 340 (M+H)⁺;

HPLC retention time (min): 4.16; HPLC condition: B.

Example 2(87) 2-(2-pyrrolidinoethylamino)-4-(perhydroazepin-1-yl)quinazoline

NMR (DMSO-d₆): δ 7.81 (d, J=8.4 Hz, 1H), 7.44 (m, 1H), 7.25 (d, J=7.8Hz, 1H), 6.96 (t, J=7.5 Hz, 1H), 6.29 (m, 1H), 3.81 (m, 4H), 3.39 (m,2H), 2.56 (t, J=6.9 Hz, 2H), 2.37 (m, 4H), 1.86 (m, 4H), 1.67 (m, 4H),1.56 (m, 4H);

MS (m/z): 340 (M+H)⁺, 215;

HPLC retention time (min): 4.41; HPLC condition: B.

Example 2(88)2-(2-piperidinoethylamino)-4-(perhydroazepin-1-yl)quinazoline

NMR (DMSO-d₆): δ 7.81 (d, J=8.4 Hz, 1H), 7.44 (m, 1H), 7.25 (d, J=8.4Hz, 1H), 6.92 (t, J=8.4 Hz, 1H), 6.23 (m, 1H), 3.86 (m, 4H), 3.38 (m,2H), 2.43 (m, 2H), 2.36 (m, 4H), 1.86 (m, 4H), 1.56 (m, 4H), 1.48 (m,4H), 1.37 (m, 2H);

MS (m/z): 354 (M+H)⁺;

HPLC retention time (min): 3.96; HPLC condition: B.

Example 2(89)2-(3-dimethylaminopropylamino)-4-(perhydroazepin-1-yl)quinazoline

NMR (DMSO-d₆): δ 7.80 (d, J=7.5 Hz, 1H), 7.48 (m, 1H), 7.24 (d, J=7.8Hz, 1H), 6.95 (t, J=7.5 Hz, 1H), 6.49 (m, 1H), 3.80 (m, 4H), 3.30 (m,2H), 2.24 (t, J=6.9 Hz, 2H), 2.11 (s, 6H), 1.86 (m, 4H), 1.62 (m, 2H),1.56 (m, 4H);

MS (m/z): 328 (M+H)⁺;

HPLC retention time (min): 2.96; HPLC condition: A.

Example 2(90)2-(4-dimethylaminobutylamino)-4-(perhydroazepin-1-yl)quinazoline

NMR (DMSO-d₆): δ 7.81 (d, J=8.1 Hz, 1H), 7.44 (t, J=8.1 Hz, 1H), 7.24(d, J=8.1 Hz, 1H), 6.96 (t, J=8.1 Hz, 1H), 6.57 (m, 1H), 3.81 (m, 4H),3.30 (m, 2H), 2.37 (m, 2H), 2.21 (s, 6H), 1.86 (m, 4H), 1.56 (m, 4H),1.50 (m, 4H);

MS (m/z): 342 (M+H)⁺;

HPLC retention time (min): 3.00; HPLC condition: A.

Example 2(91)4-(2-dimethylaminoethylamino)-2-(perhydroazepin-1-yl)quinazoline

TLC: Rf 0.31 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 7.89 (d, J=6.9 Hz, 1H), 7.83 (t, J=6.3 Hz, 1H), 7.43(dd, J=8.4, 6.9 Hz, 1H), 7.21 (d, J=7.8 Hz, 1H), 6.98 (dd, J=8.4, 7.8Hz, 1H), 3.74 (t, J=6.0 Hz, 4H), 3.57 (dt, J=6.3, 6.3 Hz, 2H), 2.54 (t,J=6.3 Hz, 2H), 2.22 (s, 6H), 1.71 (m, 4H), 1.46 (m, 4H).

Example 2(92) 2-(2-aminoethylamino)-4-(perhydroazepin-1-yl)quinazoline

TLC: Rf 0.14 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 7.81 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 7.2 Hz, 1H),7.25 (d, J=8.4 Hz, 1H), 6.96 (dd, J=8.4, 7.2 Hz, 1H), 6.46 (br, 1H),3.79 (m, 4H), 3.29 (m, 2H), 2.69 (t, J=6.0 Hz, 2H), 1.85 (m, 4H), 1.56(m, 4H).

Example 2(93)2-(2-dimethylaminoethylamino)-4-(perhydroazocin-1-yl)quinazoline

TLC: Rf 0.31 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.61 (m, 6H), 1.90 (m, 4H), 2.60 (s, 6H), 2.98 (t,J=6.18 Hz, 2H), 3.65 (t, J=6.18 Hz, 2H), 3.94 (m, 4H), 7.17 (m, 1H),7.42 (m, 1H), 7.57 (m, 1H), 7.96 (d, J=8.24 Hz, 1H).

Example 2(94) 4-(3-azabicyclo[3.2.2]nonan-3-yl)-2-(2-dimethylaminoethylamino)quinazoline

TLC: Rf 0.34 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 2.01 (m, 10H), 2.56 (s, 6H), 2.77 (t, J=6.73 Hz, 2H),3.74 (m, 2H), 4.17 (m, 4H), 6.71 (m, 1H), 7.37 (t, J=8.1 Hz, 1H), 7.65(d, J=8.1 Hz, 1H), 7.83 (t, J=8.1 Hz, 1H), 8.09 (d, J=8.10 Hz, 1H).

Example 2(95)2-(2-dimethylaminoethylamino)-4-(perhydroazepin-1-yl)quinazoline

TLC: Rf 0.45 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.56 (m, 4H), 1.85 (m, 4H), 2.16 (s, 6H), 2.39 (t,J=6.87 Hz, 2H), 3.37 (m, 2H), 3.80 (m, 4H), 6.23 (m, 1H), 6.96 (m, 1H),7.25 (d, J=8.24 Hz, 1H), 7.44 (m, 1H), 7.81 (d, J=8.52 Hz, 1H).

Reference Example 32-[1-(t-butoxycarbonyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

The title compound having the following physical data was given bysubstituting N,N-dimethylethylenediamine in example 1 with1-(t-butoxycarbonyl)pyrrolidin-2-ylmethylamine.

TLC: Rf 0.45 (chloroform:methanol=9:1);

NMR (CDCl₃): δ 7.65 (m, 1H), 5.81 (d, J=6.3 Hz, 1H), 4.01 (m, 1H), 3.52(m, 8H), 1.89 (m, 4H), 1.75 (m, 4H), 1.55 (m, 4H), 1.46 (s, 9H);

MS (m/z): 376 (M+H)⁺.

Example 32-(pyrrolidin-2-yl]methylamino)-4-(perhydroazepin-1-yl)pyrimidine

To the compound prepared in Reference Example 3 (1.06 g) was added a 95%aqueous solution of trifluoroacetic acid (20 mL) with ice cooling andthe mixture was stirred for 2 hours at 0° C. The reaction mixture wasconcentrated and the residue was purified by column chromatography onsilica gel (chloroform:methanol=9:1→chloroform:methanol:28% ammoniawater=80:10:1) to give the compound of the present invention (0.72 g)having the following physical data.

TLC: Rf 0.08 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CDCl₃): δ 1.48 (m, 6H), 1.73 (m, 4H), 2.07 (m, 2H), 2.76 (m, 2H),3.02 (m, 2H), 3.14 (m, 2H), 3.55 (m, 3H), 3.89 (m, 1H), 4.84 (d, J=6.30Hz, 1H), 5.78 (d, J=6.30 Hz, 1H), 7.79 (d, J=6.30 Hz, 1H);

MS (FAB, Pos., Glycerin+m-NBA) (m/z): 276 (M+H)⁺.

Example 42-(1-benzylpyrrolidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

A mixture of the compound prepared in Reference Example 1 (4.00 g) and1-benzyl-3-aminopyrrolidine (4.33 g) was stirred for 16 hours at 90° C.The resulting solution was cooled and purified by column chromatographyon silica gel (ethyl acetate:hexane=1:2→chloroform:methanol:28% ammoniawater=80:10:0.6) to give the title compound (4.85 g) having thefollowing physical data.

TLC: Rf 0.45 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.50 (m, 4H), 1.74 (m, 5H), 2.21 (m, 1H), 2.60 (dd,J=9.89, 5.22 Hz, 1H), 2.70 (m, 1H), 2.83 (m, 1H), 3.00 (dd, J=9.89, 6.87Hz, 1H), 3.55 (m, 4H), 3.78 (s, 2H), 4.33 (m, 1H), 5.93 (d, J=6.32 Hz,1H), 6.35 (m, 1H), 7.31 (m, 5H), 7.73 (d, J=6.04 Hz, 1H).

Example 5 4-(perhydroazepin-1-yl)-2-(pyrrolidin-3-ylamino)pyrimidine

Under atmosphere of argon to a solution of the compound prepared inExample 4 (4.5 g) in ethanol (150 mL) was added palladium hydroxide(0.97 g), and under atmosphere of hydrogen the mixture was stirred for 4hours at 75° C. The reaction mixture was cooled and filtered, and thefiltrate was concentrated. The residue was purified by columnchromatography on silica gel (methylene chloride:methanol:28% ammoniawater=80:10:0.5→80:10:1) to give the compound of the present invention(2.96 g) having the following physical data.

TLC: Rf 0.15 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.45 (m, 4H), 1.62 (m, 6H), 1.93 (m, 1H), 2.66 (dd,J=11.26, 4.40 Hz, 1H), 2.76 (m, 1H), 2.94 (m, 2H), 3.59 (m, 4H), 4.16(m, 1H), 5.85 (d, J=6.04 Hz, 1H), 6.42 (m, 1H), 7.72 (d, J=6.04 Hz, 1H).

Reference Example 42-(1-benzyloxycarbonylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

A mixture of the compound prepared in Reference Example 1 (5.74 g) and1-benzyloxycarbonyl-3-aminopiperidine (6.35 g) was stirred for 16 hoursat 90° C. The reaction mixture was cooled and purified by columnchromatography on silica gel (ethylacetate:hexane=1:2→chloroform:methanol:28% ammonia water=80:10:0.5) togive the title compound (3.40 g) having the following physical data.

TLC: Rf 0.68 (chloroform:methanol:28% ammonia water=80:10:1)

NMR (CDCl₃): δ 1.40 (m, 2H), 1.55 (m, 4H), 1.69 (m, 4H), 2.05 (m, 2H),3.05 (m, 2H), 3.55 (m, 4H), 3.91 (m, 1H), 4.12 (m, 2H), 4.73 (m, 1H),5.13 (s, 2H), 5.80 (d, J=6.00 Hz, 1H), 7.34 (m, 5H), 7.80 (d, J=6.00 Hz,1H).

Example 6 2-(piperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

Under atmosphere of argon, to a solution of the compound prepared inReference Example 4 (5.06 g) in methanol (150 mL) was addedpalladium-carbon (1.0 g) and under atmosphere of hydrogen the mixturewas stirred for 4 hours at room temperature. The reaction mixture wasfiltered and the filtrate was concentrated. The residue was purified bycolumn chromatography on silica gel (methylene chloride:methanol:28%ammonia water=80:10:0.5→80:10:1) to give the compound of the presentinvention (3.02 g) having the following physical data.

TLC: Rf 0.18 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CDCl₃): δ 1.48 (m, 6H), 1.73 (m, 4H), 2.07 (m, 2H), 2.76 (m, 2H),3.02 (m, 2H), 3.14 (m, 2H), 3.55 (m, 3H), 3.89 (m, 1H), 4.84 (d, J=6.30Hz, 1H), 5.78 (d, J=6.30 Hz, 1H), 7.79 (d, J=6.30 Hz, 1H).

Example 6(1) 4-(perhydroazepin-1-yl)-2-(piperidin-4-ylamino)pyrimidine

By the same procedure as described in Example 6 using correspondingcompounds, the compound of the present invention having the followingphysical data was given.

TLC: Rf 0.15 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.27 (m, 2H), 1.45 (m, 4H), 1.65 (m, 4H), 1.76 (m, 2H),2.47 (m, 2H), 2.92 (m, 2H), 3.63 (m, 5H), 5.81 (d, J=6.04 Hz, 1H), 6.19(m, 1H), 7.70 (d, J=6.04 Hz, 1H).

Example 72-[1-(3-methylbutyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

To a solution of the compound prepared in Example 3 (200 mg) in a 1%solution of acetic acid in N,N-dimethylformamide (3 mL) were added3-methylbutanal (93.4 mg) and sodium triacetoxyborohydride (462 mg) andthe mixture was stirred for 8 hours at room temperature. To the reactionmixture was added acetic acid (0.5 mL). The resulting solution waspoured into PS-sulfonic acid resin (prewashed with methanol (5 mL×3times), Argonaut Inc. product ID:800287, lot. No. 00819, 1.43 mmol/g,2.06 g). The resin was washed with methanol (5 mL×3 times).Subsequently, the resin was eluted with 5% triethylamine-methanolsolution (30 mL) and the eluted solution was concentrated. The resin wasdissolved in methylene chloride (10 mL) and thereto was added isocyanateresin (Argonaut Inc., product ID:800262, lot. No. 00814, 1.43 mmol/g,1.00 g) and the resulting mixture was subjected to a reaction. Thereaction mixture was filtered and the filtrate was concentrated to givethe compound of the present invention (85 mg) having the followingphysical data.

TLC: Rf 0.43 (dichloromethane:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆, 373 K): δ 0.79 (d, J=6.60 Hz, 3H), 0.80 (m, J=6.60 Hz,3H), 1.34 (m, 2H), 1.43 (m, 4H), 1.63 (m, 7H), 1.82 (m, 2H), 2.45 (m,2H), 2.89 (m, 2H), 3.16 (m, 2H), 3.42 (m, 1H), 3.50 (t, J=5.70 Hz, 4H),5.83 (d, J=6.20 Hz, 1H), 6.02 (m, 1H), 7.66 (d, J=6.20 Hz, 1H);

HPLC retention time (min): 4.53; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(1) to Example 7(375)

By the same procedure as described in Reference Example 1→ReferenceExample 3→Example 3→Example 7, Reference Example 1→Example 4→Example5→Example 7 or Reference Example 1→Reference Example 4→Example 6→Example7 using corresponding compounds, the compounds of the present inventionhaving the following compounds were given.

Example 7(1)2-[1-(4-methylbenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.54 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CD₃OD): δ 1.53 (m, 4H), 1.69 (m, 6H), 2.30 (s, 3H), 2.43 (dd,J=10.03, 5.08 Hz, 1H), 2.57 (m, 1H), 2.70 (m, 1H), 2.92 (dd, J=9.89,7.14 Hz, 1H), 3.61 (m, 4H), 4.37 (m, 1H), 4.86 (s, 2H), 5.90 (d, J=6.32Hz, 1H), 7.16 (m, 4H), 7.65 (d, J=6.32 Hz, 1H).

Example 7(2)2-[1-(3-methoxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.85 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.43 (m, 4H), 1.68 (m, 6H), 2.10 (m, 1H), 2.28 (dd,J=9.34, 5.49 Hz, 1H), 2.48 (m, 1H), 2.79 (t, J=8.10 Hz, 1H), 3.33 (s,3H), 3.51 (m, 4H), 3.71 (s, 2H), 4.21 (m, 1H), 5.81 (m, 1H), 6.44 (s,1H), 6.81 (m, 3H), 7.19 (m, 1H), 7.69 (m, 1H).

Example 7(3)2-(1-cyclohexylmethylpyrrolidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.77 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆, 373.1K): δ 0.94 (m, 2H), 1.20 (m, 3H), 1.46 (m, 5H), 1.67(m, 10H), 2.10 (m, 1H), 2.24 (m, 2H), 2.37 (dd, J=9.34, 5.22 Hz, 1H),2.48 (m, 1H), 2.59 (m, 1H), 2.80 (dd, J=9.07, 6.87 Hz, 1H), 3.56 (t,J=6.00 Hz, 4H), 4.26 (m, 1H), 5.77 (m, 1H), 5.84 (d, J=6.04 Hz, 1H),7.72 (d, J=6.04 Hz, 1H).

Example 7(4)2-[(3S)-1-isobutylpyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.70 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 0.84 (d, J=6.59 Hz, 6H), 1.44 (m, 4H), 1.62 (m, 5H),2.09 (m, 4H), 2.25 (dd, J=9.34, 5.49 Hz, 1H), 2.45 (m, 2H), 2.77 (t,J=9.00 Hz, 1H), 3.38 (m, 4H), 4.19 (m, 1H), 5.83 (d, J=6.04 Hz, 1H),6.37 (m, 1H), 7.71 (d, J=6.04 Hz, 1H).

Example 7(5)2-[(3R)-1-isobutylpyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.70 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 0.84 (d, J=6.59 Hz, 6H), 1.44 (m, 4H), 1.62 (m, 5H),2.09 (m, 4H), 2.25 (dd, J=9.34, 5.49 Hz, 1H), 2.45 (m, 2H), 2.77 (t,J=9.00 Hz, 1H), 3.38 (m, 4H), 4.19 (m, 1H), 5.83 (d, J=6.04 Hz, 1H),6.37 (m, 1H), 7.71 (d, J=6.04 Hz, 1H).

Example 7(6)2-[1-(2,4,6-trimethoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.13; MS (m/z): 911 (2M+H)⁺, 456 (M+H)⁺; HPLCcondition: B.

Example 7(7)2-[1-(3-cyanobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.94; MS (m/z): 781 (2M+H)⁺, 391 (M+H)⁺; HPLCcondition: B.

Example 7(8)2-[1-(3-methylbutyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.34; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(9)2-[1-(2-carboxymethyloxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.04; MS (m/z): 879 (2M+H)⁺, 440 (M+H)⁺; HPLCcondition: B.

Example 7(10)2-[1-(4-dimethylaminobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.20; MS (m/z): 817 (2M+H)⁺, 409 (M+H)⁺, 134;HPLC condition: B.

Example 7(11)2-[1-(3-phenoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.50; MS (m/z): 915 (2M+H)⁺, 458 (M+H)⁺; HPLCcondition: B.

Example 7(12)2-(1-carboxymethylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 2.81; MS (m/z): 667 (2M+H)⁺, 334 (M+H)⁺; HPLCcondition: B.

Example 7(13)2-[1-(cyclopropylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.98; MS (m/z): 659 (2M+H)⁺, 330 (M+H)⁺; HPLCcondition: B.

Example 7(14)2-[1-(3-methylthiopropyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.93; MS (m/z): 364 (M+H)⁺; HPLC condition:B.

Example 7(15)2-[1-(quinolin-2-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.92; MS (m/z): 833 (2M+H)⁺, 417 (M+H)⁺; HPLCcondition: B.

Example 7(16)2-[1-[(Z)-dec-4-enyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.53; MS (m/z): 827 (2M+H)⁺, 414 (M+H)⁺,207.5; HPLC condition: A.

Example 7(17)2-[1-(3-phenylpropyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.34; MS (m/z): 787 (2M+H)⁺, 394 (M+H)⁺; HPLCcondition: B.

Example 7(18)2-(1-butylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.23; MS (m/z): 332 (M+H)⁺; HPLC condition:B.

Example 7(19)2-(1-benzylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.13; MS (m/z): 731 (2M+H)⁺, 366 (M+H)⁺; HPLCcondition: B.

Example 7(20)2-[1-[(E)-3-(4-dimethylaminophenyl)-2-propenyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.36; MS (m/z): 869 (2M+H)⁺, 435 (M+H)⁺, 160;HPLC condition: B.

Example 7(21)2-[1-[(E)-3-(2-furyl)-2-propenyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.03; MS (m/z): 763 (2M+H)⁺, 382 (M+H)⁺; HPLCcondition: B.

Example 7(22)2-[1-(3-hydroxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.43; MS (m/z): 763 (2M+H)⁺, 382 (M+H)⁺; HPLCcondition: B.

Example 7(23)2-[1-(2-hydroxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.11; MS (m/z): 763 (2M+H)⁺, 382 (M+H)⁺; HPLCcondition: B.

Example 7(24)2-[1-(4-dihydroxyborylbenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.09; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(25)2-[1-(4-heptyloxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.70; MS (m/z): 959 (2M+H)⁺, 480 (M+H)⁺; HPLCcondition: A.

Example 7(26)2-[1-(benzo[b]furan-2-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.14; MS (m/z): 811 (2M+H)⁺, 406 (M+H)⁺; HPLCcondition: B.

Example 7(27)2-[1-(3-methylbenzo[b]thiophen-2-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 871 (2M+H)⁺, 436 (M+H)⁺; HPLCcondition: B.

Example 7(28)2-[1-(3,7-dimethyloct-6-enyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.48; MS (m/z): 827 (2M+H)⁺, 414 (M+H)⁺,207.5; HPLC condition: A.

Example 7(29)2-[1-(4-pyrrolidinobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 869 (2M+H)⁺, 435 (M+H)⁺, 160;HPLC condition: B.

Example 7(30)2-[1-[3-(4-t-butylphenyl)-2-methylpropyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.58; MS (m/z): 927 (2M+H)⁺, 464 (M+H)⁺,232.5; HPLC condition: A.

Example 7(31)2-[1-(2-benzyloxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.48; MS (m/z): 943 (2M+H)⁺, 472 (M+H)⁺; HPLCcondition: B.

Example 7(32)2-[1-[3,5-di-(t-butyl)-4-hydroxybenzyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.76; MS (m/z): 987 (2M+H)⁺, 494 (M+H)⁺; HPLCcondition: B.

Example 7(33)2-[1-[3-(4-isopropylphenyl)-2-methylpropyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.06; MS (m/z): 899 (2M+H)⁺, 450 (M+H)⁺; HPLCcondition: B.

Example 7(34)2-[1-[3,4-bis(benzyloxy)benzyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.52; MS (m/z): 578 (M+H)⁺; HPLC condition:B.

Example 7(35)2-[1-(3-octyloxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.81; MS (m/z): 987 (2M+H)⁺, 494 (M+H)⁺, 276,219; HPLC condition: A.

Example 7(36)2-[1-(3,5,5-trimethylhexyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.43; MS (m/z): 803 (2M+H)⁺, 402 (M+H)⁺,201.5; HPLC condition: A.

Example 7(37)2-[1-[5-(4-hydroxy-4-methylpentyl)-1,2,3,4-tetrahydrobenzen-2-ylmethyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.42; MS (m/z): 939 (2M+H)⁺, 470 (M+H)⁺; HPLCcondition: B.

Example 7(38)2-[1-(5-hydroxypentyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.50; MS (m/z): 362 (M+H)⁺; HPLC condition:B.

Example 7(39)2-[1-[(1R,2S,3R,5R)-2-hydroxy-4,6,8-trioxaspiro[bicyclo[3.3.0]octane-7,1′-cyclohexane]-3-ylmethyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.81; MS (m/z): 975 (2M+H)⁺, 488 (M+H)⁺, 290;HPLC condition: B.

Example 7(40)2-[1-(3-phenylpyrazol-4-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.76; MS (m/z): 863 (2M+H)⁺, 432 (M+H)⁺, 290;HPLC condition: B.

Example 7(41)2-[1-(4-t-butylbenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.68; MS (m/z): 843 (2M+H)⁺, 422 (M+H)⁺; HPLCcondition: B.

Example 7(42)2-[1-(benzo-1,4-dioxan-6-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.98; MS (m/z): 847 (2M+H)⁺, 424 (M+H)⁺; HPLCcondition: B.

Example 7(43)2-[1-[2-(1,1,5-trimethyl-1,2,3,4-tetrahydrobenzen-6-yl)ethyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.48; MS (m/z): 851 (2M+H)⁺, 426 (M+H)⁺; HPLCcondition: A.

Example 7(44)2-[1-[4-(3-dimethylaminopropyloxy)benzyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.17; MS (m/z): 933 (2M+H)⁺, 467 (M+H)⁺; HPLCcondition: B.

Example 7(45)2-[1-(2-furylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.82; MS (m/z): 711 (2M+H)⁺, 356 (M+H)⁺; HPLCcondition: B.

Example 7(46)2-(1-isobutylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.29; MS (m/z): 663 (2M+H)⁺, 332 (M+H)⁺; HPLCcondition: B.

Example 7(47)2-(1-cyclohexylmethylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.86; MS (m/z): 743 (2M+H)⁺, 372 (M+H)⁺; HPLCcondition: B.

Example 7(48)2-[1-(2-thiazolylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.65; MS (m/z): 745 (2M+H)⁺, 373 (M+H)⁺; HPLCcondition: B.

Example 7(49)2-[1-(4-acetylaminobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.56; MS (m/z): 845 (2M+H)⁺, 423 (M+H)⁺; HPLCcondition: B.

Example 7(50)2-[1-(2-methoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.13; MS (m/z): 791 (2M+H)⁺, 396 (M+H)⁺; HPLCcondition: B.

Example 7(51)2-[1-(4-methoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 791 (2M+H)⁺, 396 (M+H)⁺; HPLCcondition: B.

Example 7(52)2-[1-(4-phenylbenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.55; MS (m/z): 883 (2M+H)⁺, 442 (M+H)⁺; HPLCcondition: B.

Example 7(53)2-[1-[(2E)-3,7-dimethyloct-2,6-dienyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.95; MS (m/z): 823 (2M+H)⁺, 412 (M+H)⁺; HPLCcondition: B.

Example 7(54)2-[1-(4-diethylaminobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.55; MS (m/z): 873 (2M+H)⁺, 437 (M+H)⁺, 162;HPLC condition: B.

Example 7(55)2-[1-(2-ethylhexyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.36; MS (m/z): 775 (2M+H)⁺, 388 (M+H)⁺, 276,194; HPLC condition: A.

Example 7(56)2-[1-(3-fluorobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.18; MS (m/z): 767 (2M+H)⁺, 384 (M+H)⁺; HPLCcondition: B.

Example 7(57)2-[1-(2-hydroxyethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.29; MS (m/z): 320 (M+H)⁺; HPLC condition:B.

Example 7(58)2-[1-(1-naphthylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.54; MS (m/z): 831 (2M+H)⁺, 416 (M+H)⁺; HPLCcondition: B.

Example 7(59)2-[1-(3-nitrobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.08; MS (m/z): 821 (2M+H)⁺, 411 (M+H)⁺; HPLCcondition: B.

Example 7(60)2-(1-propylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.01; MS (m/z): 635 (2M+H)⁺, 318 (M+H)⁺; HPLCcondition: B.

Example 7(61)2-[1-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.11; MS (m/z): 819 (2M+H)⁺, 410 (M+H)⁺; HPLCcondition: B.

Example 7(62)2-[1-(2-thienomethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.05; MS (m/z): 743 (2M+H)⁺, 372 (M+H)⁺; HPLCcondition: B.

Example 7(63)2-[1-(4-chlorobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.35; MS (m/z): 801 (2M+H)⁺, 400 (M+H)⁺; HPLCcondition: B.

Example 7(64)2-[1-(2,3-dimethoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.08; MS (m/z): 426 (M+H)⁺; HPLC condition:B.

Example 7(65)2-[1-[(3S,4R)-3,4,5-trihydroxypentyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.18; MS (m/z): 787 (2M+H)⁺, 394 (M+H)⁺; HPLCcondition: B.

Example 7(66)2-[1-(1,5-dimethyl-2-phenyl-3-oxo-2,3-dihydro-1H-pyrazol-4-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.52; MS (m/z): 951 (2M+H)⁺, 476 (M+H)⁺; HPLCcondition: B.

Example 7(67)2-[1-[5-[(E)-4-methylpent-2-enyl]-1,2,3,4-tetrahydrobenzen-2-ylmethyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.57; MS (m/z): 903 (2M+H)⁺, 452 (M+H)⁺, 276;HPLC condition: A.

Example 7(68)2-[1-(4-hexyloxy-3-methoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.76; MS (m/z): 991 (2M+H)⁺, 496 (M+H)⁺; HPLCcondition: B.

Example 7(69)2-[1-(4-fluorobenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.16; MS (m/z): 767 (2M+H)⁺, 384 (M+H)⁺; HPLCcondition: B.

Example 7(70)2-[1-(1,2,5-trimethyl-1,2,3,4-tetrahydrobenzen-3-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.11; MS (m/z): 823 (2M+H)⁺, 412 (M+H)⁺; HPLCcondition: B.

Example 7(71)2-[1-(3,5-dimethyl-1-phenylpyrazol-4-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.04; MS (m/z): 919 (2M+H)⁺, 460 (M+H)⁺; HPLCcondition: B.

Example 7(72)2-[1-(2-benzyloxyethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(73)2-[1-(4-benzyloxy-3-methoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.29; MS (m/z): 502 (M+H)⁺; HPLC condition:B.

Example 7(74)2-[1-(3-benzyloxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.45; MS (m/z): 943 (2M+H)⁺, 472 (M+H)⁺; HPLCcondition: B.

Example 7(75)2-[1-(4-benzyloxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.44; MS (m/z): 943 (2M+H)⁺, 472 (M+H)⁺; HPLCcondition: B.

Example 7(76)2-[1-(4-phenoxybenzyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.51; MS (m/z): 915 (2M+H)⁺, 458 (M+H)⁺; HPLCcondition: B.

Example 7(77)2-[2-[N-methyl-N-(2,4,6-trimethoxybenzyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.16; MS (m/z): 430 (M+H)⁺, 416; HPLCcondition: B.

Example 7(78)2-[2-[N-methyl-N-(3-methylbutyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.26; MS (m/z): 320 (M+H)⁺; HPLC condition:B.

Example 7(79)2-[2-[N-(2-carboxymethyloxybenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 2.97; MS (m/z): 827 (2M+H)⁺, 414 (M+H)⁺; HPLCcondition: B.

Example 7(80)2-[2-[N-(4-dimethylaminobenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.11; MS (m/z): 383 (M+H)⁺, 134; HPLCcondition: B.

Example 7(81)2-[2-(N-carboxymethyl-N-methylamino)ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 2.77; MS (m/z): 615 (2M+H)⁺, 308 (M+H)⁺; HPLCcondition: B.

Example 7(82) 2-[2-(N-cyclopropylmethyl-N-methylamino)ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.88; MS (m/z): 304 (M+H)⁺; HPLC condition:B.

Example 7(83)2-[2-[N-methyl-N-(3-methylthiopropyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.86; MS (m/z): 338 (M+H)⁺; HPLC condition:B.

Example 7(84)2-[2-[N-(3-carboxypropyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 2.81; MS (m/z): 671 (2M+H)⁺, 336 (M+H)⁺; HPLCcondition: B.

Example 7(85)2-[2-[N-(2,6-dimethylhept-5-enyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.84; MS (m/z): 374 (M+H)⁺; HPLC condition:B.

Example 7(86)2-[2-[N-(2,2-dimethylpropyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.41; MS (m/z): 320 (M+H)⁺; HPLC condition:B.

Example 7(87)2-[2-[N-[(Z)-dec-4-enyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.13; MS (m/z): 388 (M+H)⁺; HPLC condition:B.

Example 7(88)2-[2-[N-methyl-N-(3-phenylpropyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.22; MS (m/z): 368 (M+H)⁺; HPLC condition:B.

Example 7(89)2-[2-(N-butyl-N-methylamino)ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.11; MS (m/z): 306 (M+H)⁺; HPLC condition:B.

Example 7(90) 2-[2-(N-benzyl-N-methylamino)ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.05; MS (m/z): 340 (M+H)⁺; HPLC condition:B.

Example 7(91)2-[2-[N-[(E)-3-(4-dimethylaminophenyl)-2-propenyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.26; MS (m/z): 817 (2M+H)⁺, 409 (M+H)⁺; HPLCcondition: B.

Example 7(92) 2-[2-[N-(E)-3-(2-furyl)-2-propenyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.95; MS (m/z): 356 (M+H)⁺; HPLC condition:B.

Example 7(93)2-[2-[N-(3-hydroxybenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.44; MS (m/z): 356 (M+H)⁺, 262; HPLCcondition: B.

Example 7(94)2-[2-[N-(2-hydroxybenzyl)-N-methylaminoethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.95; MS (m/z): 711 (2M+H)⁺, 356 (M+H)⁺; HPLCcondition: B.

Example 7(95) 2-[2-[3-N-(4-heptyloxybenzyl)-N-methylaminoethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.11; MS (m/z): 454 (M+H)⁺; HPLC condition:B.

Example 7(96)2-[2-[N-(3,7-dimethyloct-6-enyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.98; MS (m/z): 388 (M+H)⁺; HPLC condition:B.

Example 7(97)2-[2-[N-methyl-N-(4-pyrrolidinobenzyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.46; MS (m/z): 409 (M+H)⁺, 160; HPLCcondition: B.

Example 7(98)2-[2-[N-[3-(4-t-butylphenyl)-2-methylpropyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.99; MS (m/z): 438 (M+H)⁺; HPLC condition:B.

Example 7(99)2-[2-[N-(2-benzyloxybenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 446 (M+H)⁺; HPLC condition:B.

Example 7(100)2-[2-[N-[3-(4-isopropylphenyl)-2-methylpropyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.89; MS (m/z): 424 (M+H)⁺; HPLC condition:B.

Example 7(101)2-[2-[N-[3,4-bis(benzyloxy)benzyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.10; MS (m/z): 552 (M+H)⁺; HPLC condition:B.

Example 7(102)2-[2-[N-(4-octyloxybenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.71; MS (m/z): 468 (M+H)⁺, 219; HPLCcondition: A.

Example 7(103)2-[2-[N-methyl-N-(3,5,5-trimethylhexyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.98; MS (m/z): 376 (M+H)⁺; HPLC condition:B.

Example 7(104)2-[2-[N-[5-(4-hydroxy-4-methylpentyl)-1,2,3,4-tetrahydrobenzen-2-ylmethyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.27; MS (m/z): 444 (M+H)⁺; HPLC condition:B.

Example 7(105)2-[2-[N-(5-hydroxypentyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.43; MS (m/z): 336 (M+H)⁺; HPLC condition:B.

Example 7(106)2-[2-[N-methyl-N-(3-phenylpyrazol-4-ylmethyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.68; MS (m/z): 811 (2M+H)⁺, 406 (M+H)⁺, 278;HPLC condition: B.

Example 7(107)2-[2-[N-(4-t-butylbenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.57; MS (m/z): 396 (M+H)⁺; HPLC condition:B.

Example 7(108)2-[2-[N-(benzo-1,4-dioxan-6-ylmethyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.91; MS (m/z): 795 (2M+H)⁺, 398 (M+H)⁺, 292;HPLC condition: B.

Example 7(109)2-[2-[N-methyl-N-[2-(1,1,5-trimethyl-1,2,3,4-tetrahydrobenzen-6-yl)ethyl]amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.03; MS (m/z): 400 (M+H)⁺, 118; HPLCcondition: B.

Example 7(110)2-[2-[N-(2-furylmethyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.78; MS (m/z): 330 (M+H)⁺, 250; HPLCcondition: B.

Example 7(111)2-[2-[N-(4-diethylaminobenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.45; MS (m/z): 411 (M+H)⁺, 162; HPLCcondition: B.

Example 7(112)2-[2-[N-(2-ethylhexyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.94; MS (m/z): 362 (M+H)⁺; HPLC condition:B.

Example 7(113)2-[2-[N-methyl-N-(naphthalen-1-ylmethyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.36; MS (m/z): 390 (M+H)⁺; HPLC condition:B.

Example 7(114)2-[2-(N-methyl-N-propylamino)ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.92; MS (m/z): 292 (M+H)⁺; HPLC condition:B.

Example 7(115)4-(perhydroazepin-1-yl)-2-[2-[N-methyl-N-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]amino]ethylamino]pyrimidine

HPLC retention time (min): 3.08; MS (m/z): 384 (M+H)⁺; HPLC condition:B.

Example 7(116)2-[2-[N-(2,3-dimethoxybenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.00; MS (m/z): 400 (M+H)⁺, 118; HPLCcondition: B.

Example 7(117)2-[2-[N-methyl-N-[(3S,4R)-3,4,5-trihydroxypentyl]amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.13; MS (m/z): 735 (2M+H)⁺, 368 (M+H)⁺; HPLCcondition: B.

Example 7(118)2-[2-[N-(1,5-dimethyl-2-phenyl-3-oxo-2,3-dihydro-1H-pyrazol-4-ylmethyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.48; MS (m/z): 450 (M+H)⁺; HPLC condition:B.

Example 7(119)2-[2-[N-[5-[(E)-4-methylpent-2-enyl]-1,2,3,4-tetrahydrobenzen-2-ylmethyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.50; MS (m/z): 426 (M+H)⁺, 358, 208; HPLCcondition: A.

Example 7(120)2-[2-[N-methyl-N-(1,2,5-trimethyl-1,2,3,4-tetrahydrobenzen-3-ylmethyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.88; MS (m/z): 386 (M+H)⁺; HPLC condition:B.

Example 7(121)2-[2-[N-(3,5-dimethyl-1-phenylpyrazol-4-ylmethyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.95; MS (m/z): 867 (2M+H)⁺, 434 (M+H)⁺; HPLCcondition: B.

Example 7(122)2-[2-[N-(4-benzyloxy-3-methoxybenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.21; MS (m/z): 951 (2M+H)⁺, 476 (M+H)⁺; HPLCcondition: B.

Example 7(123)2-[2-[N-(4-benzyloxybenzyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.35; MS (m/z): 446 (M+H)⁺; HPLC condition:B.

Example 7(124)2-[1-(2,4,6-trimethoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.86; MS (m/z): 456 (M+H)⁺; HPLC condition:B.

Example 7(125)2-[1-(2-carboxymethyloxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.04; MS (m/z): 879 (2M+H)⁺, 440 (M+H)⁺; HPLCcondition: B.

Example 7(126)2-[1-(4-dimethylaminobenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.38; MS (m/z): 409 (M+H)⁺, 134; HPLCcondition: B.

Example 7(127)2-[1-(3-phenoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.58; MS (m/z): 458 (M+H)⁺; HPLC condition:B.

Example 7(128)2-[1-[(E)-2-methyl-2-butenyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.50; MS (m/z): 344 (M+H)⁺; HPLC condition:B.

Example 7(129)2-(1-carboxymethylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 2.83; MS (m/z): 667 (2M+H)⁺, 334 (M+H)⁺; HPLCcondition: B.

Example 7(130)2-(1-cyclopropylmethylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.11; MS (m/z): 330 (M+H)⁺; HPLC condition:B.

Example 7(131)2-[1-(3-methylthiopropyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 364 (M+H)⁺, 276; HPLCcondition: B.

Example 7(132)2-[1-(2,6-dimethyl-hept-5-enyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.34; MS (m/z): 400 (M+H)⁺, 276, 200.5; HPLCcondition: A.

Example 7(133)2-(1-neopentylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.71; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(134)2-[1-[(Z)-dec-4-enyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.49; MS (m/z): 414 (M+H)⁺, 207.5; HPLCcondition: A.

Example 7(135)2-[1-(3-phenylpropyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.46; MS (m/z): 394 (M+H)⁺; HPLC condition:B.

Example 7(136)2-(1-butylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.36; MS (m/z): 332 (M+H)⁺; HPLC condition:B.

Example 7(137)2-(1-benzylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.26; MS (m/z): 366 (M+H)⁺; HPLC condition:B.

Example 7(138)2-[1-[(E)-3-(4-dimethylaminophenyl)-2-propenyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.54; MS (m/z): 435 (M+H)⁺, 160; HPLCcondition: B.

Example 7(139)2-[1-[(E)-3-(2-furyl)-2-propenyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.15; MS (m/z): 382 (M+H)⁺; HPLC condition:B.

Example 7(140)2-[1-(3-hydroxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.62; MS (m/z): 763 (2M+H)⁺, 382 (M+H)⁺; HPLCcondition: B.

Example 7(141)2-[1-(2-hydroxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.12; MS (m/z): 382 (M+H)⁺, 276; HPLCcondition: B.

Example 7(142)2-[1-(4-dihydroxyborylbenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.20; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(143)2-[1-(4-heptyloxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.62; MS (m/z): 480 (M+H)⁺, 276; HPLCcondition: A.

Example 7(144)2-[1-(3-methylbenzo[b]thiophen-2-ylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.63; MS (m/z): 436 (M+H)⁺; HPLC condition:B.

Example 7(145)2-[1-(3,7-dimethyloct-6-enyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.43; MS (m/z): 414 (M+H)⁺, 207.5; HPLCcondition: A.

Example 7(146)2-[1-(4-pyrrolidinobenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.83; MS (m/z): 435 (M+H)⁺; HPLC condition:B.

Example 7(147)2-[1-[3-(4-t-butylphenyl)-2-methylpropyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.53; MS (m/z): 464 (M+H)⁺, 232.5; HPLCcondition: A.

Example 7(148)2-[1-(2-benzyloxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.58; MS (m/z): 472 (M+H)⁺; HPLC condition:B.

Example 7(149)2-[1-[3-(4-isopropylphenyl)-2-methylpropyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.46; MS (m/z): 450 (M+H)⁺, 225.5; HPLCcondition: A.

Example 7(150)2-[1-[3,4-bis(benzyloxy)benzyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.72; MS (m/z): 578 (M+H)⁺; HPLC condition:B.

Example 7(151)2-[1-[5-(4-hydroxy-4-methylpentyl)-1,2,3,4-tetrahydrobenzen-2-ylmethyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.58; MS (m/z): 470 (M+H)⁺; HPLC condition:B.

Example 7(152)2-[1-(5-hydroxypentyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.58; MS (m/z): 362 (M+H)⁺; HPLC condition:B.

Example 7(153)2-[1-[(1R,2S,3R,5R)-2-hydroxy-4,6,8-trioxaspiro[bicyclo[3.3.0]octane-7,1′-cyclohexane]-3-ylmethyl]pyrrolidin-2-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.99; MS (m/z): 488 (M+H)⁺, 276; HPLCcondition: B.

Example 7(154)2-[1-(3-phenylpyrazol-4-ylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.79; MS (m/z): 863 (2M+H)⁺, 432 (M+H)⁺, 290;HPLC condition: B.

Example 7(155)2-[1-(4-t-butylbenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.83; MS (m/z): 422 (M+H)⁺; HPLC condition:B.

Example 7(156)2-[1-(1,4-benzodioxan-6-ylmethyl)pyrrolidin-2-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.13; MS (m/z): 424 (M+H)⁺, 276; HPLCcondition: B.

Example 7(157)2-[1-[2-(1,1,5-trimethyl-1,2,3,4-tetrahydrobenzen-6-yl)ethyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.41; MS (m/z): 426 (M+H)⁺, 276, 213.5; HPLCcondition: A.

Example 7(158)2-[1-[4-(3,3-dimethylaminopropyloxy)benzyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.36; MS (m/z): 467 (M+H)⁺, 234; HPLCcondition: B.

Example 7(159)2-[1-(2-furylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.94; MS (m/z): 356 (M+H)⁺; HPLC condition:B.

Example 7(160)2-(1-isobutylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.48; MS (m/z): 332 (M+H)⁺; HPLC condition:B.

Example 7(161)2-(1-cyclohexylmethylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.06; MS (m/z): 372 (M+H)⁺; HPLC condition:B.

Example 7(162)2-[1-(4-acetylaminobenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.65; MS (m/z): 845 (2M+H)⁺, 423 (M+H)⁺; HPLCcondition: B.

Example 7(163)2-[1-(2-methoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.32; MS (m/z): 396 (M+H)⁺; HPLC condition:B.

Example 7(164)2-[1-(4-methoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.19; MS (m/z): 396 (M+H)⁺; HPLC condition:B.

Example 7(165)2-[1-(4-phenylbenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.66; MS (m/z): 442 (M+H)⁺; HPLC condition:B.

Example 7(166)2-[1-[(2E)-3,7-dimethyloct-2,6-dienyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.40; MS (m/z): 412 (M+H)⁺, 276; HPLCcondition: A.

Example 7(167)2-[1-(4-diethylaminobenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.78; MS (m/z): 437 (M+H)⁺, 162; HPLCcondition: B.

Example 7(168)2-[1-(2-ethylhexyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.31; MS (m/z): 388 (M+H)⁺, 194.5; HPLCcondition: A.

Example 7(169)2-[1-(naphthalen-1-ylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 416 (M+H)⁺; HPLC condition:B.

Example 7(170)2-(1-propylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.14; MS (m/z): 318 (M+H)⁺; HPLC condition:B.

Example 7(171)4-(perhydroazepin-1-yl)-2-[1-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pyrrolidin-2-ylmethylamino]pyrimidine

HPLC retention time (min): 3.18; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(172)2-[1-(2-thienylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.15; MS (m/z): 372 (M+H)⁺, 276; HPLCcondition: B.

Example 7(173)2-[1-(4-chlorobenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.47; MS (m/z): 400 (M+H)⁺; HPLC condition:B.

Example 7(174)2-[1-(2,3-dimethoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.25; MS (m/z): 426 (M+H)⁺; HPLC condition:B.

Example 7(175)4-(perhydroazepin-1-yl)-2-[1-[(3S,4R)-3,4,5-trihydroxypentyl]pyrrolidin-2-ylmethylamino]pyrimidine

HPLC retention time (min): 3.21; MS (m/z): 787 (2M+H)⁺, 394 (M+H)⁺; HPLCcondition: B.

Example 7(176)2-[1-(1,5-dimethyl-2-phenyl-3-oxo-2,3-dihydro-1H-pyrazol-4-ylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.68; MS (m/z): 476 (M+H)⁺; HPLC condition:B.

Example 7(177)2-[1-[5-[(E)-4-methyl-2-pentenyl]-1,2,3,4-tetrahydrobenzen-2-ylmethyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.53; MS (m/z): 452 (M+H)⁺, 384, 226.5; HPLCcondition: A.

Example 7(178)2-[1-(4-hexyloxy-3-methoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.86; MS (m/z): 496 (M+H)⁺; HPLC condition:B.

Example 7(179)2-[1-(4-fluorobenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.27; MS (m/z): 384 (M+H)⁺; HPLC condition:B.

Example 7(180)2-[1-(1,2,5-trimethyl-1,2,3,4-tetrahydrobenzen-3-ylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.32; MS (m/z): 412 (M+H)⁺, 206.5; HPLCcondition: A.

Example 7(181)2-[1-(3,5-dimethyl-1-phenylpyrazol-4-ylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.15; MS (m/z): 460 (M+H)⁺; HPLC condition:B.

Example 7(182)2-[1-(4-benzyloxy-3-methoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.40; MS (m/z): 502 (M+H)⁺; HPLC condition:B.

Example 7(183)2-[1-(3-benzyloxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 472 (M+H)⁺; HPLC condition:B.

Example 7(184)2-[1-(4-benzyloxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.57; MS (m/z): 472 (M+H)⁺; HPLC condition:B.

Example 7(185)2-[1-(4-phenoxybenzyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.63; MS (m/z): 458 (M+H)⁺; HPLC condition:B.

Example 7(186)2-[2-[N-[(E)-2-butenyl]-N-methyl]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.98; MS (m/z): 304 (M+H)⁺; HPLC condition:B.

Example 7(187)2-[2-(N-methyl-N-pentyl)ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.35; MS (m/z): 320 (M+H)⁺; HPLC condition:B.

Example 7(188)2-[2-[N-methyl-N-[(E)-2-pentenyl]amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.18; MS (m/z): 318 (M+H)⁺; HPLC condition:B.

Example 7(189)2-[2-[N-(2-ethylbutyl)-N-methyl]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.55; MS (m/z): 334 (M+H)⁺; HPLC condition:B.

Example 7(190)2-[2-(N-hexyl-N-methyl)ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 334 (M+H)⁺; HPLC condition:B.

Example 7(191)2-[2-[N-methyl-N-(2-methylpentyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 334 (M+H)⁺; HPLC condition:B.

Example 7(192)2-[2-[N-[(E)-2-hexenyl]-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 332 (M+H)⁺; HPLC condition:B.

Example 7(193)2-[2-[N-(3,3-dimethylbutyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 334 (M+H)⁺; HPLC condition:B.

Example 7(194)2-[2-[N-(1,2,3,4-tetrahydrobenzen-2-ylmethyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 344 (M+H)⁺; HPLC condition:B.

Example 7(195)2-[2-[N-(2,3-dimethylpentyl)-N-methylamino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.71; MS (m/z): 348 (M+H)⁺; HPLC condition:B.

Example 7(196)2-[2-[N-methyl-(N-2-octynyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.47; MS (m/z): 358 (M+H)⁺; HPLC condition:B.

Example 7(197)2-[2-[N-methyl-N-(2-propylpentyl)amino]ethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.96; MS (m/z): 362 (M+H)⁺; HPLC condition:B.

Example 7(198)2-[1-(2-methoxyethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.68; MS (m/z): 334 (M+H)⁺; HPLC condition:B.

Example 7(199)2-[1-[(E)-2-butenyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.23; MS (m/z): 330 (M+H)⁺; HPLC condition:B.

Example 7(200)2-(1-pentylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.62; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(201)2-[1-[(E)-2-pentenyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.45; MS (m/z): 344 (M+H)⁺; HPLC condition:B.

Example 7(202)2-[1-(2-ethylbutyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.91; MS (m/z): 360 (M+H)⁺; HPLC condition:B.

Example 7(203)2-(1-hexylpyrrolidin-2-ylmethylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.91; MS (m/z): 360 (M+H)⁺; HPLC condition:B.

Example 7(204)2-[1-(2-methylpentyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.93; MS (m/z): 360 (M+H)⁺; HPLC condition:B.

Example 7(205)2-[1-[(E)-2-hexenyl]pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.68; MS (m/z): 358 (M+H)⁺; HPLC condition:B.

Example 7(206)2-[1-(3,3-dimethylbutyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.65; MS (m/z): 360 (M+H)⁺; HPLC condition:B.

Example 7(207)2-[1-(1,2,3,4-tetrahydrobenzen-2-ylmethyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.71; MS (m/z): 370 (M+H)⁺; HPLC condition:B.

Example 7(208)2-[1-(2,3-dimethylpentyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.11; MS (m/z): 374 (M+H)⁺; HPLC condition:B.

Example 7(209)2-[1-(2-octynyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.68; MS (m/z): 384 (M+H)⁺; HPLC condition:B.

Example 7(210)2-[1-(2-propylpentyl)pyrrolidin-2-ylmethylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.94; MS (m/z): 388 (M+H)⁺; HPLC condition:B.

Example 7(211)2-[1-(2-methoxyethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.53; MS (m/z): 320 (M+H)⁺; HPLC condition:B.

Example 7(212)2-[1-[(E)-2-butenyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 316 (M+H)⁺; HPLC condition:B.

Example 7(213)2-[1-(2,2-dimethoxyethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.51; MS (m/z): 350 (M+H)⁺; HPLC condition:B.

Example 7(214)2-(1-pentylpyrrolidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.39; MS (m/z): 332 (M+H)⁺; HPLC condition:B.

Example 7(215)2-[1-[(E)-2-pentenyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.24; MS (m/z): 330 (M+H)⁺; HPLC condition:B.

Example 7(216)2-[1-(2-ethylbutyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(217)2-(1-hexylpyrrolidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.63; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(218)2-[1-(2-methylpentyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.56; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(219)2-[1-[(E)-2-hexenyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.45; MS (m/z): 344 (M+H)⁺; HPLC condition:B.

Example 7(220)2-[1-(3,3-dimethylbutyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.44; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(221)2-[1-(1,2,3,4-tetrahydrobenzen-2-ylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.39; MS (m/z): 356 (M+H)⁺; HPLC condition:B.

Example 7(222)2-[1-(2,3-dimethylpentyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.70; MS (m/z): 360 (M+H)⁺; HPLC condition:B.

Example 7(223)2-[1-(2,2-dimethyl-4-pentenyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.62; MS (m/z): 358 (M+H)⁺; HPLC condition:B.

Example 7(224)2-[1-(2-octynyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.53; MS (m/z): 370 (M+H)⁺; HPLC condition:B.

Example 7(225)2-[1-(2-propylpentyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.97; MS (m/z): 374 (M+H)⁺; HPLC condition:B.

Example 7(226)2-[1-(2-methoxyethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.56; MS (m/z): 334 (M+H)⁺; HPLC condition:B.

Example 7(227)2-[1-[(E)-2-butenyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.10; MS (m/z): 659 (2M+H)⁺, 330 (M+H)⁺; HPLCcondition: B.

Example 7(228)2-[1-(2,2-dimethoxyethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.56; MS (m/z): 364 (M+H)⁺; HPLC condition:B.

Example 7(229)2-(1-pentylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.45; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(230)2-[1-[(E)-2-pentenyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.29; MS (m/z): 344 (M+H)⁺; HPLC condition:B.

Example 7(231)2-[1-(2-ethylbutyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

TLC: Rf 0.60 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CDCl₃): δ 0.84 (t, J=7.5 Hz, 6H), 1.31 (m, 5H), 1.54 (m, 6H), 1.75(m, 6H), 2.11 (d, J=7.0 Hz, 2H), 2.22 (m, 1H), 2.32 (m, 2H), 2.67 (m,1H), 3.56 (m, 4H), 4.02 (m, 1H), 5.32 (m, 1H), 5.77 (d, J=6.0 Hz, 1H),7.77 (d, J=6.0 Hz, 1H); HPLC retention time (min): 4.77; MS (m/z): 719(2M+H)⁺, 360 (M+H)⁺; HPLC condition: B.

Example 7(232)2-(1-hexylpiperidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.73; MS (m/z): 719 (2M+H)⁺, 360 (M+H)⁺; HPLCcondition: B.

Example 7(233)2-[1-(2-methylpentyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.77; MS (m/z): 719 (2M+H)⁺, 360 (M+H)⁺; HPLCcondition: B.

Example 7(234)2-[1-[(E)-2-hexenyl]piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.51; MS (m/z): 358 (M+H)⁺; HPLC condition:B.

Example 7(235)2-[1-(3,3-dimethylbutyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.50; MS (m/z): 360 (M+H)⁺; HPLC condition:B.

Example 7(236)2-[1-(1,2,3,4-tetrahydrobenzen-2-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.54; MS (m/z): 739 (2M+H)⁺, 370 (M+H)⁺; HPLCcondition: B.

Example 7(237)2-[1-(2,3-dimethylpentyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.96; MS (m/z): 747 (2M+H)⁺, 374 (M+H)⁺; HPLCcondition: B.

Example 7(238)2-[1-(2-octynyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.59; MS (m/z): 384 (M+H)⁺; HPLC condition:B.

Example 7(239)2-[1-(2-propylpentyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.09; MS (m/z): 775 (2M+H)⁺, 388 (M+H)⁺; HPLCcondition: B.

Example 7(240)4-(perhydroazepin-1-yl)-2-[1-(2,4,6-trimethoxybenzyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.19; MS (m/z): 442 (M+H)⁺; HPLC condition:B.

Example 7(241)2-[1-(3-cyanobenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.86; MS (m/z): 753 (2M+H)⁺, 377 (M+H)⁺; HPLCcondition: B.

Example 7(242)2-[1-(3-methylbutyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.33; MS (m/z): 332 (M+H)⁺; HPLC condition:B.

Example 7(243)2-[1-(2-carboxymethyloxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.00; MS (m/z): 851 (2M+H)⁺, 426 (M+H)⁺; HPLCcondition: B.

Example 7(244)2-[1-(4-dimethylaminobenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.00; MS (m/z): 395 (M+H)⁺; HPLC condition:B.

Example 7(245)4-(perhydroazepin-1-yl)-2-[1-(3-phenoxybenzyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 444 (M+H)⁺; HPLC condition:B.

Example 7(246)2-[1-[(E)-2-methyl-2-butenyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.21; MS (m/z): 330 (M+H)⁺; HPLC condition:B.

Example 7(247)2-[1-[(1R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.87; MS (m/z): 396 (M+H)⁺; HPLC condition:B.

Example 7(248)2-[1-[(Z)-4-decenyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.34; MS (m/z): 400 (M+H)⁺; HPLC condition:B.

Example 7(249)4-(perhydroazepin-1-yl)-2-[1-(3-phenylpropyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.30; MS (m/z): 380 (M+H)⁺; HPLC condition:B.

Example 7(250)2-(1-butylpyrrolidin-3-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.19; MS (m/z): 318 (M+H)⁺; HPLC condition:B.

Example 7(251)2-[1-[(E)-3-(4-dimethylaminophenyl)-2-propenyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.01; MS (m/z): 421 (M+H)⁺; HPLC condition:B.

Example 7(252)2-[1-(3-hydroxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.38; MS (m/z): 735 (2M+H)⁺, 368 (M+H)⁺; HPLCcondition: B.

Example 7(253)2-[1-(2-hydroxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.97; MS (m/z): 735 (2M+H)⁺, 368 (M+H)⁺; HPLCcondition: B.

Example 7(254)2-[1-(4-dihydroxyborylbenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.03; MS (m/z): 396 (M+H)⁺; HPLC condition:B.

Example 7(255)2-[1-(4-heptyloxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.16; MS (m/z): 466 (M+H)⁺, 398; HPLCcondition: B.

Example 7(256)2-[1-(benzo[b]furan-2-ylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.08; MS (m/z): 392 (M+H)⁺; HPLC condition:B.

Example 7(257)2-[1-(3-methylbenzo[b]thiophen-2-ylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 843 (2M+H)⁺, 422 (M+H)⁺; HPLCcondition: B.

Example 7(258)2-[1-[2-(4-chlorophenylthio)benzyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.85; MS (m/z): 496, 494(M+H)⁺, 398; HPLCcondition: B.

Example 7(259)2-[1-(3,7-dimethyl-6-octenyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.10; MS (m/z): 400 (M+H)⁺; HPLC condition:B.

Example 7(260)4-(perhydroazepin-1-yl)-2-[1-(4-pyrrolidinobenzyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.46; MS (m/z): 421 (M+H)⁺; HPLC condition:B.

Example 7(261)2-[1-[2-methyl-3-(4-t-butylphenyl)propyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.03; MS (m/z): 450 (M+H)⁺; HPLC condition:B.

Example 7(262)2-[1-(2-benzyloxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 458 (M+H)⁺; HPLC condition:B.

Example 7(263)2-[1-[3,5-di-(t-butyl)-4-hydroxybenzyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.63; MS (m/z): 480 (M+H)⁺; HPLC condition:B.

Example 7(264)2-[1-[3-(4-isopropylphenyl)-2-methylpropyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.94; MS (m/z): 436 (M+H)⁺; HPLC condition:B.

Example 7(265)2-[1-[3,4-bis(benzyloxy)benzyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.48; MS (m/z): 564 (M+H)⁺; HPLC condition:B.

Example 7(266)4-(perhydroazepin-1-yl)-2-[1-(3,5,5-trimethylhexyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 5.11; MS (m/z): 388 (M+H)⁺; HPLC condition:B.

Example 7(267)2-[1-(butoxycarbonylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.91; MS (m/z): 376 (M+H)⁺, 260; HPLCcondition: B.

Example 7(268)2-[1-[5-(4-hydroxy-4-methylpentyl)-1,2,3,4-tetrahydrobenzen-2-ylmethyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.26; MS (m/z): 456 (M+H)⁺; HPLC condition:B.

Example 7(269)2-[1-(5-hydroxypentyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.45; MS (m/z): 348 (M+H)⁺; HPLC condition:B.

Example 7(270)2-[1-[(1R,2S,3R,5R)-2-hydroxy-4,6,8-trioxaspiro[bicyclo[3.3.0]octane-7,1′-cyclohexane]-3-ylmethyl]pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.77; MS (m/z): 474 (M+H)⁺; HPLC condition:B.

Example 7(271)4-(perhydroazepin-1-yl)-2-[1-(3-phenylpyrazol-4-ylmethyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 3.69; MS (m/z): 835 (2M+H)⁺, 418 (M+H)⁺; HPLCcondition: B.

Example 7(272)2-[1-(4-t-butylbenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.54; MS (m/z): 408 (M+H)⁺; HPLC condition:B.

Example 7(273)2-[1-(1,4-benzodioxan-6-ylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.88; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(274)4-(perhydroazepin-1-yl)-2-[1-[2-(1,1,5-trimethyl-1,2,3,4-tetrahydrobenzen-6-yl)ethyl]pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 5.23; MS (m/z): 412 (M+H)⁺; HPLC condition:B.

Example 7(275)4-(perhydroazepin-1-yl)-2-[1-[4-(3-dimethylaminopropyloxy)benzyl]pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.08; MS (m/z): 453 (M+H)⁺; HPLC condition:B.

Example 7(276)2-[1-(2-furylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.78; MS (m/z): 342 (M+H)⁺; HPLC condition:B.

Example 7(277)4-(perhydroazepin-1-yl)-2-[1-(2-thiazolylmethyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 3.56; MS (m/z): 359 (M+H)⁺; HPLC condition:B.

Example 7(278)2-[1-(4-acetylaminobenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.47; MS (m/z): 817 (2M+H)⁺, 409 (M+H)⁺; HPLCcondition: B.

Example 7(279)2-[1-(2-methoxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 382 (M+H)⁺; HPLC condition:B.

Example 7(280)2-[1-(4-methoxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.95; MS (m/z): 382 (M+H)⁺; HPLC condition:B.

Example 7(281)4-(perhydroazepin-1-yl)-2-[1-(4-phenylbenzyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.41; MS (m/z): 855 (2M+H)⁺, 428 (M+H)⁺; HPLCcondition: B.

Example 7(282)2-[1-((2E)-3,7-dimethyl-2,6-octadienyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.94; MS (m/z): 398 (M+H)⁺; HPLC condition:B.

Example 7(283)2-[1-(4-diethylaminobenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.44; MS (m/z): 423 (M+H)⁺; HPLC condition:B.

Example 7(284)2-[1-(2-ethylhexyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.99; MS (m/z): 374 (M+H)⁺; HPLC condition:B.

Example 7(285)2-[1-(3-fluorobenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.04; MS (m/z): 370 (M+H)⁺; HPLC condition:B.

Example 7(286)2-[1-(2-hydroxyethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.27; MS (m/z): 306 (M+H)⁺; HPLC condition:B.

Example 7(287)2-[1-(1-naphthylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.33; MS (m/z): 402 (M+H)⁺; HPLC condition:B.

Example 7(288)2-[1-(3-nitrobenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.93; MS (m/z): 793 (2M+H)⁺, 397 (M+H)⁺; HPLCcondition: B.

Example 7(289)4-(perhydroazepin-1-yl)-2-[1-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 3.07; MS (m/z): 791 (2M+H)⁺, 396 (M+H)⁺; HPLCcondition: B.

Example 7(290)4-(perhydroazepin-1-yl)-2-[1-(2-thienylmethyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 3.95; MS (m/z): 358 (M+H)⁺; HPLC condition:B.

Example 7(291)2-[1-(4-chlorobenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.21; MS (m/z): 388, 386 (M+H)⁺; HPLCcondition: B.

Example 7(292) 2-[1-(1,3-benzodioxol-4-ylmethyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.93; MS (m/z): 396 (M+H)⁺; HPLC condition:B.

Example 7(293)4-(perhydroazepin-1-yl)-2-[1-((3S,4R)-3,4,5-trihydroxypentyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 3.14; MS (m/z): 759 (2M+H)⁺, 380 (M+H)⁺; HPLCcondition: B.

Example 7(294)2-[1-(1,5-dimethyl-2-phenyl-3-oxo-2,3-dihydro-1H-pyrazol-4-ylmethyl)piperidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.49; MS (m/z): 923 (2M+H)⁺, 462 (M+H)⁺; HPLCcondition: B.

Example 7(295)4-(perhydroazepin-1-yl)-2-[1-[5-[(E)-4-methyl-2-pentenyl]-1,2,3,4-tetrahydrobenzen-2-yl]pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 5.43; MS (m/z): 438 (M+H)⁺; HPLC condition:B.

Example 7(296)2-[1-(3-methoxy-4-hexyloxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.59; MS (m/z): 963 (2M+H)⁺, 482 (M+H)⁺; HPLCcondition: B.

Example 7(297)4-(perhydroazepin-1-yl)-2-[1-(4-fluorobenzyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.02; MS (m/z): 370 (M+H)⁺; HPLC condition:B.

Example 7(298)4-(perhydroazepin-1-yl)-2-[1-(1,2,5-trimethyl-1,2,3,4-tetrahydrobenzen-3-ylmethyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.98; MS (m/z): 398 (M+H)⁺; HPLC condition:B.

Example 7(299)4-(perhydroazepin-1-yl)-2-[1-(3,5-dimethyl-1-phenylpyrazol-4-ylmethyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 3.91; MS (m/z): 891 (2M+H)⁺, 446 (M+H)⁺; HPLCcondition: B.

Example 7(300)2-[1-(4-benzyloxy-3-methoxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.19; MS (m/z): 975 (2M+H)⁺, 488 (M+H)⁺; HPLCcondition: B.

Example 7(301)2-[1-(3-benzyloxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.33; MS (m/z): 458 (M+H)⁺; HPLC condition:B.

Example 7(302)2-[1-(4-benzyloxybenzyl)pyrrolidin-3-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.32; MS (m/z): 915 (2M+H)⁺, 458 (M+H)⁺; HPLCcondition: B.

Example 7(303)4-(perhydroazepin-1-yl)-2-[1-(4-phenoxybenzyl)pyrrolidin-3-ylamino]pyrimidine

HPLC retention time (min): 4.41; MS (m/z): 887 (2M+H)⁺, 444 (M+H)⁺; HPLCcondition: B.

Example 7(304)4-(perhydroazepin-1-yl)-2-[1-(2,4,6-trimethoxybenzyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 4.13; MS (m/z): 911 (2M+H)⁺, 456 (M+H)⁺; HPLCcondition: B.

Example 7(305)2-[1-(3-cyanobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.95; MS (m/z): 781 (2M+H)⁺, 391 (M+H)⁺; HPLCcondition: B.

Example 7(306)2-[1-(3-methylbutyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.33; MS (m/z): 346 (M+H)⁺; HPLC condition:B.

Example 7(307)2-[1-(2-carboxymethoxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.03; MS (m/z): 879 (2M+H)⁺, 440 (M+H)⁺; HPLCcondition: B.

Example 7(308)2-[1-(4-dimethylaminobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.19; MS (m/z): 817 (2M+H)⁺, 409 (M+H)⁺; HPLCcondition: B.

Example 7(309)4-(perhydroazepin-1-yl)-2-[1-(3-phenoxybenzyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 4.50; MS (m/z): 915 (2M+H)⁺, 458 (M+H)⁺; HPLCcondition: B.

Example 7(310)2-[1-[(E)-2-methyl-2-butenyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.37; MS (m/z): 687 (2M+H)⁺, 344 (M+H)⁺; HPLCcondition: B.

Example 7(311)2-[(1R)-1-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.09; MS (m/z): 819 (2M+H)⁺, 410 (M+H)⁺; HPLCcondition: B.

Example 7(312)2-[1-carboxymethylpiperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 2.78; MS (m/z): 667 (2M+H)⁺, 334 (M+H)⁺; HPLCcondition: B.

Example 7(313)2-(1-cyclopropylmethylpiperidin-4-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.97; MS (m/z): 659 (2M+H)⁺, 330 (M+H)⁺; HPLCcondition: B.

Example 7(314)2-[1-(3-methylthiopropyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.95; MS (m/z): 364 (M+H)⁺; HPLC condition:B.

Example 7(315)2-[1-(2,6-dimethyl-5-heptenyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.03; MS (m/z): 799 (2M+H)⁺, 400 (M+H)⁺; HPLCcondition: B.

Example 7(316)4-(perhydroazepin-1-yl)-2-[1-(quinolin-2-ylmethyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 3.93; MS (m/z): 833 (2M+H)⁺, 417 (M+H)⁺; HPLCcondition: B.

Example 7(317)2-(1-neopentylpiperidin-4-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.76; MS (m/z): 691 (2M+H)⁺, 346 (M+H)⁺; HPLCcondition: B.

Example 7(318)2-[1-[(Z)-4-decenyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.34; MS (m/z): 414 (M+H)⁺; HPLC condition:B.

Example 7(319)4-(perhydroazepin-1-yl)-2-[1-(3-phenylpropyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 4.32; MS (m/z): 787 (2M+H)⁺, 394 (M+H)⁺; HPLCcondition: B.

Example 7(320)2-[1-butylpiperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.21; MS (m/z): 332 (M+H)⁺; HPLC condition:B.

Example 7(321)2-[1-[(E)-3-(4-dimethylaminophenyl)-2-propenyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.33; MS (m/z): 869 (2M+H)⁺, 435 (M+H)⁺; HPLCcondition: B.

Example 7(322)2-[1-(3-hydroxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.44; MS (m/z): 763 (2M+H)⁺, 382 (M+H)⁺; HPLCcondition: B.

Example 7(323)2-[1-(2-hydroxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.10; MS (m/z): 763 (2M+H)⁺, 382 (M+H)⁺; HPLCcondition: B.

Example 7(324)2-[1-(4-dihydroxyborylbenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.11; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(325)2-[1-(4-heptyloxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.31; MS (m/z): 480 (M+H)⁺; HPLC condition:B.

Example 7(326)2-[1-(benzo[b]furan-2-ylmethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.17; MS (m/z): 811 (2M+H)⁺, 406 (M+H)⁺; HPLCcondition: B.

Example 7(327)2-[1-(3-methylbenzo[b]thiophen-2-yl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.54; MS (m/z): 871 (2M+H)⁺, 436 (M+H)⁺; HPLCcondition: B.

Example 7(328)2-[1-[2-(4-chlorophenylthio)benzyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.03; MS (m/z): 510, 508 (M+H)⁺; HPLCcondition: B.

Example 7(329)2-[1-(3,7-dimethyl-6-octenyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.12; MS (m/z): 414 (M+H)⁺; HPLC condition:B.

Example 7(330)4-(perhydroazepin-1-yl)-2-[1-(4-pyrrolidinobenzyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 4.57; MS (m/z): 869 (2M+H)⁺, 435 (M+H)⁺; HPLCcondition: B.

Example 7(331)2-[1-[2-methyl-3-(4-t-butylphenyl)propyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.21; MS (m/z): 464 (M+H)⁺; HPLC condition:B.

Example 7(332)2-[1-(2-benzyloxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.44; MS (m/z): 472 (M+H)⁺; HPLC condition:B.

Example 7(333)2-[1-(3,5-di-t-butyl-4-hydroxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.72; MS (m/z): 494 (M+H)⁺; HPLC condition:B.

Example 7(334)2-[1-[3-(4-isopropylphenyl)-2-methylpropyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.09; MS (m/z): 450 (M+H)⁺; HPLC condition:B.

Example 7(335)2-[1-[3,4-bis(benzyloxy)benzyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.57; MS (m/z): 578 (M+H)⁺; HPLC condition:B.

Example 7(336)2-[1-(4-octyloxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 5.64; MS (m/z): 494 (M+H)⁺; HPLC condition:B.

Example 7(337)4-(perhydroazepin-1-yl)-2-[1-(3,5,5-trimethylhexyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 5.16; MS (m/z): 402 (M+H)⁺; HPLC condition:B.

Example 7(338)2-(1-butoxycarbonylmethylpiperidin-4-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.99; MS (m/z): 779 (2M+H)⁺, 390 (M+H)⁺; HPLCcondition: B.

Example 7(339)2-[1-[5-(4-hydroxy-4-methylpentyl)-1,2,3,4-tetrahydrobenzen-2-ylmethyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.41; MS (m/z): 470 (M+H)⁺; HPLC condition:B.

Example 7(340)2-[1-(5-hydroxypentyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.49; MS (m/z): 723 (2M+H)⁺, 362 (M+H)⁺; HPLCcondition: B.

Example 7(341)2-[1-[(1R,2S,3R,5R)-2-hydroxy-4,6,8-trioxaspiro[bicyclo[3.3.0]octane-7,1′-cyclohexane]-3-ylmethyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.80; MS (m/z): 488 (M+H)⁺; HPLC condition:B.

Example 7(342)4-(perhydroazepin-1-yl)-2-[1-(3-phenylpyrazol-4-ylmethyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 3.77; MS (m/z): 863 (2M+H)⁺, 432 (M+H)⁺; HPLCcondition: B.

Example 7(343)2-[1-(4-t-butylbenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.68; MS (m/z): 843 (2M+H)⁺, 422 (M+H)⁺; HPLCcondition: B.

Example 7(344)2-[1-(1,4-benzodioxan-6-ylmethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.99; MS (m/z): 847 (2M+H)⁺, 424 (M+H)⁺; HPLCcondition: B.

Example 7(345)4-(perhydroazepin-1-yl)-2-[1-[2-(1,1,5-trimethyl-1,2,3,4-tetrahydrobenzen-6-yl)ethyl]piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 5.18; MS (m/z): 426 (M+H)⁺; HPLC condition:B.

Example 7(346)2-[1-[4-(3-dimethylaminopropyloxy)benzyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.22; MS (m/z): 467 (M+H)⁺; HPLC condition:B.

Example 7(347)2-[1-(2-furylmethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.82; MS (m/z): 711 (2M+H)⁺, 356 (M+H)⁺; HPLCcondition: B.

Example 7(348)2-(1-isobutylpiperidin-4-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.30; MS (m/z): 663 (2M+H)⁺, 332 (M+H)⁺; HPLCcondition: B.

Example 7(349)2-(1-cyclohexylmethylpiperidin-4-ylamino)-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.85; MS (m/z): 743 (2M+H)⁺, 372 (M+H)⁺; HPLCcondition: B.

Example 7(350)4-(perhydroazepin-1-yl)-2-[1-(2-thiazolylmethyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 3.64; MS (m/z): 745 (2M+H)⁺, 373 (M+H)⁺; HPLCcondition: B.

Example 7(351)2-[1-(4-acetylaminobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.55; MS (m/z): 845 (2M+H)⁺, 423 (M+H)⁺; HPLCcondition: B.

Example 7(352)2-[1-(2-methoxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.13; MS (m/z): 791 (2M+H)⁺, 396 (M+H)⁺; HPLCcondition: B.

Example 7(353)2-[1-(4-methoxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 791 (2M+H)⁺, 396 (M+H)⁺; HPLCcondition: B.

Example 7(354)4-(perhydroazepin-1-yl)-2-[1-(4-phenylbenzyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 4.54; MS (m/z): 883 (2M+H)⁺, 442 (M+H)⁺; HPLCcondition: B.

Example 7(355)2-[1-[(2E)-3,7-dimethyl-2,6-octadienyl]piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.89; MS (m/z): 823 (2M+H)⁺, 412 (M+H)⁺; HPLCcondition: B.

Example 7(356)2-[1-(4-diethylaminobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.57; MS (m/z): 873 (2M+H)⁺, 437 (M+H)⁺; HPLCcondition: B.

Example 7(357)2-[1-(3-fluorobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.15; MS (m/z): 767 (2M+H)⁺, 384 (M+H)⁺; HPLCcondition: B.

Example 7(358)2-[1-(1-naphthylmethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.54; MS (m/z): 831 (2M+H)⁺, 416 (M+H)⁺; HPLCcondition: B.

Example 7(359)2-[1-(3-nitrobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.04; MS (m/z): 821 (2M+H)⁺, 411 (M+H)⁺; HPLCcondition: B.

Example 7(360)4-(perhydroazepin-1-yl)-2-(1-propylpiperidin-4-ylamino)pyrimidine

HPLC retention time (min): 4.02; MS (m/z): 635 (2M+H)⁺, 318 (M+H)⁺; HPLCcondition: B.

Example 7(361)4-(perhydroazepin-1-yl)-2-[1-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 3.14; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(362)4-(perhydroazepin-1-yl)-2-[1-(2-thienylmethyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 743 (2M+H)⁺, 372 (M+H)⁺; HPLCcondition: B.

Example 7(363)2-[1-(4-chlorobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.35; MS (m/z): 799 (2M+H)⁺, 402, 400 (M+H)⁺;HPLC condition: B.

Example 7(364)2-[1-(1,3-benzodioxol-4-yl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.02; MS (m/z): 819 (2M+H)⁺, 410 (M+H)⁺; HPLCcondition: B.

Example 7(365)4-(perhydroazepin-1-yl)-2-[1-[(3S,4R)-3,4,5-trihydroxypentyl]piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 3.18; MS (m/z): 787 (2M+H)⁺, 394 (M+H)⁺; HPLCcondition: B.

Example 7(366)2-[1-(1,5-dimethyl-2-phenyl-3-oxo-2,3-dihydro-1H-pyrazol-4-ylmethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 3.51; MS (m/z): 951 (2M+H)⁺, 476 (M+H)⁺; HPLCcondition: B.

Example 7(367)2-[1-(3-methoxy-4-hexyloxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.72; MS (m/z): 496 (M+H)⁺; HPLC condition:B.

Example 7(368)2-[1-(4-fluorobenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.13; MS (m/z): 767 (2M+H)⁺, 384 (M+H)⁺; HPLCcondition: B.

Example 7(369)4-(perhydroazepin-1-yl)-2-[1-(1,2,5-trimethyl-1,2,3,4-tetrahydrobenzen-3-ylmethyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 5.18; MS (m/z): 823 (2M+H)⁺, 412 (M+H)⁺; HPLCcondition: B.

Example 7(370)2-[1-(3,5-dimethyl-1-phenylpyrazol-4-ylmethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.02; MS (m/z): 919 (2M+H)⁺, 460 (M+H))⁺;HPLC condition: B.

Example 7(371)2-[1-(2-benzyloxyethyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.06; MS (m/z): 410 (M+H)⁺; HPLC condition:B.

Example 7(372)2-[1-(4-benzyloxy-3-methoxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.30; MS (m/z): 502 (M+H)⁺; HPLC condition:B.

Example 7(373)2-[1-(3-benzyloxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.44; MS (m/z): 943 (2M+H)⁺, 472 (M+H)⁺; HPLCcondition: B.

Example 7(374)2-[1-(4-benzyloxybenzyl)piperidin-4-ylamino]-4-(perhydroazepin-1-yl)pyrimidine

HPLC retention time (min): 4.44; MS (m/z): 943 (2M+H)⁺, 472 (M+H)⁺; HPLCcondition: B.

Example 7(375)4-(perhydroazepin-1-yl)-2-[1-(4-phenoxybenzyl)piperidin-4-ylamino]pyrimidine

HPLC retention time (min): 4.51; MS (m/z): 915 (2M+H)⁺, 458 (M+H)⁺; HPLCcondition: B.

Example 84-(perhydroazepin-1-yl)-2-[(1-benzyl)azetidin-3-ylamino]pyrimidine

By the same procedure as described in Example 4 using the compoundprepared in Reference Example 1 and 1-benzyl-3-aminoazetidine, thecompound of the present invention having the following physical data wasgiven.

TLC: Rf 0.40 (ethyl acetate:methanol:triethylamine=20:2:1);

MS (m/z): 338 (M+H)⁺, 248, 190;

HPLC retention time (min): 3.01; HPLC condition: A.

Example 8(1) to Example 8(2)

By the same procedure as described in Example 8 using the compoundprepared in Reference Example 1 and corresponding amine compounds, thecompounds of the present invention having the following physical datawere given.

Example 8(1)4-(perhydroazepin-1-yl)-2-[(3S)-(1-benzyl)piperidin-3-ylamino]pyrimidine

TLC: Rf 0.50 (ethyl acetate:methanol:triethylamine=20:2:1);

NMR (DMSO-d₆, 323K): δ 1.33 (m, 1H), 1.45 (m, 4H), 1.51 (m, 1H), 1.65(m, 5H), 1.76 (m, 1H), 1.90 (m, 1H), 2.04 (m, 1H), 2.60 (m, 1H), 2.85(m, 1H), 3.28 (m, 2H), 3.49 (m, 4H), 3.84 (m, 1H), 5.83 (d, J=6.0 Hz,1H), 5.94 (m, 1H), 7.23 (m, 1H), 7.29 (m, 4H), 7.70 (d, J=6.0 Hz, 1H);

MS (m/z): 366 (M+H)⁺, 276;

HPLC retention time (min): 3.03; HPLC condition: A.

Example 8(2)4-(perhydroazepin-1-yl)-2-[(3S)-(1-benzyl)perhydroazepin-3-ylamino]pyrimidine

TLC: Rf 0.45 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.41 (m, 5H), 1.64 (m, 9H), 2.56 (m, 3H), 2.81 (m, 1H),3.49 (m, 4H), 3.63 (s, 2H), 3.97 (m, 1H), 5.80 (d, J=6.0 Hz, 1H), 6.06(m, 1H), 7.24 (m, 5H), 7.68 (d, J=6.0 Hz, 1H);

MS (m/z): 380 (M+H)⁺, 290;

HPLC retention time (min): 3.03; HPLC condition: A.

Example 9 4-(perhydroazepin-1-yl)-2-(azetidin-3-ylamino)pyrimidine

By the same procedure as described in Example 5 using the compoundprepared in Example 8, the compound of the present invention having thefollowing physical data was given.

TLC: Rf 0.65 (chloroform:methanol:28% ammonia water=80:20:4);

NMR (CDCl₃): δ 1.52 (m, 4H), 1.73 (m, 4H), 3.54 (m, 4H), 3.61 (m, 2H),3.89 (m, 2H), 4.85 (m, 1H), 5.41 (m, 1H), 5.80 (d, J=6.0 Hz, 1H), 7.77(d, J=6.0 Hz, 1H);

MS (m/z): 248 (M+H)⁺, 124.5 (M+2H)²⁺;

HPLC retention time (min): 2.81; HPLC condition: A.

Example 9(1) to Example 9(3)

By the same procedure as described in Example 9 using correspondingbenzylamine derivatives, the compounds of the present invention havingthe following physical data were given.

Example 9(1)4-(perhydroazepin-1-yl)-2-[(3S)-piperidin-3-ylamino]pyrimidine

TLC: Rf 0.70 (chloroform:methanol:28% ammonia water=80:20:4);

NMR (DMSO-d₆): δ 1.43 (m, 6H), 1.62 (m, 5H), 1.82 (m, 1H), 2.34 (m, 2H),2.73 (m, 1H), 3.00 (m, 1H), 3.45 (m, 4H), 3.75 (m, 1H), 5.82 (d, J=6.0Hz, 1H), 6.21 (m, 1H), 7.70 (d, J=6.0 Hz, 1H);

MS (m/z): 276 (M+H)⁺, 138.5 (M+2H)²⁺;

HPLC retention time (min): 2.85; HPLC condition: A.

Example 9(2)4-(perhydroazepin-1-yl)-2-[(3S)-perhydroazepin-3-ylamino]pyrimidine

TLC: Rf 0.33 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.34 (m, 5H), 1.70 (m, 9H), 2.60 (dd, J=13.5, 7.0 Hz,1H), 2.72 (t, J=5.5 Hz, 2H), 2.90 (dd, J=13.5, 4.0 Hz, 1H), 3.57 (m,4H), 3.90 (m, 1H), 5.81 (d, J=6.0 Hz, 1H), 6.10 (m, 1H), 7.70 (d, J=6.0Hz, 1H);

MS (m/z): 290 (M+H)⁺, 145.5 (M+2H)²⁺;

HPLC retention time (min): 2.92; HPLC condition: A.

Example 9(3)4-(perhydroazepin-1-yl)-2-[(3S)-perhydroazepin-3-ylamino]-5,6,7,8-tetrahydroquinazoline

TLC: Rf 0.32 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆): δ 1.43 (m, 6H), 1.56 (m, 5H), 1.73 (m, 7H), 2.43 (m, 4H),2.57 (m, 1H), 2.71 (t, J=6.0 Hz, 2H), 2.87 (m, 1H), 3.50 (t, J=6.0 Hz,4H), 3.85 (m, 1H), 5.85 (m, 1H);

MS (m/z): 344(M+H)⁺, 172.5 (M+2H)²⁺;

HPLC retention time (min): 3.09; HPLC condition: A.

Example 104-(perhydroazepin-1-yl)-2-[(1-isobutyl)azetidin-3-ylamino]pyrimidine

By the same procedure as described in Example 7 using the compoundprepared in Example 9 and isobutylaldehyde, the compound of the presentinvention having the following physical data was given.

TLC: Rf 0.40 (ethyl acetate:methanol:triethylamine=20:2:1);

NMR (DMSO-d₆, 323K): δ 0.84 (d, J=7.0 Hz, 6H), 1.47 (m, 4H), 1.52 (m,1H), 1.69 (m, 4H), 2.19 (d, J=7.0 Hz, 2H), 2.80 (t, J=7.0 Hz, 2H), 3.54(m, 6H), 4.33 (m, 1H), 5.87 (d, J=6.0 Hz, 1H), 6.62 (m, 1H), 7.73 (d,J=6.0 Hz, 1H);

MS (m/z): 304 (M+H)⁺, 248, 152.5 (M+2H)²⁺;

HPLC retention time (min): 2.96; HPLC condition: A.

Example 10(1) to Example 10(12)

By the same procedure as described in Example 10 using correspondingamine compounds and corresponding aldehyde compounds, the compounds ofthe present invention having the following physical data were given.

Example 10(1)4-(perhydroazepin-1-yl)-2-[1-(2-ethylbutyl)azetidin-3-ylamino]pyrimidine

TLC: Rf 0.40 (ethyl acetate:methanol:triethylamine=20:2:1);

NMR (DMSO-d₆, 323K): δ 0.82 (t, J=7.5 Hz, 6H), 1.15 (m, 1H), 1.25 (m,2H), 1.30 (m, 2H), 1.48 (m, 4H), 1.69 (m, 4H), 2.27 (d, J=6.5 Hz, 2H),2.79 (t, J=7.0 Hz, 2H), 3.53 (m, 6H), 4.32 (m, 1H), 5.87 (d, J=6.0 Hz,1H), 6.62 (m, 1H), 7.73 (d, J=6.0 Hz, 1H);

MS (m/z): 332 (M+H)⁺, 248, 166.5 (M+2H)²⁺; HPLC retention time (min):3.09; HPLC condition: A.

Example 10(2)4-(perhydroazepin-1-yl)-2-[(1-cyclohexyl)azetidin-3-ylamino]pyrimidine

TLC: Rf 0.40 (ethyl acetate:methanol:triethylamine=20:2:1);

MS (m/z): 330 (M+H)⁺, 248, 165.5 (M+2H)²⁺; HPLC retention time (min):3.03; HPLC condition: A.

Example 10(3)4-(perhydroazepin-1-yl)-2-[1-(2-pyridinylmethyl)azetidin-3-ylamino]pyrimidine

TLC: Rf 0.33 (ethyl acetate:methanol:triethylamine=20:2:1);

MS (m/z): 339 (M+H)⁺, 170 (M+2H)²⁺; HPLC retention time (min): 2.94;HPLC condition: A.

Example 10(4)4-(perhydroazepin-1-yl)-2-[(3S)-(1-isobutyl)piperidin-3-ylamino]pyrimidine

TLC: Rf 0.50 (ethyl acetate:methanol:triethylamine=20:2:1);

NMR (DMSO-d₆, 323K): δ 0.85 (d, J=6.5 Hz, 3H), 0.87 (d, J=6.5 Hz, 3H),1.33 (m, 1H), 1.48 (m, 5H), 1.69 (m, 7H), 1.88 (m, 1H), 2.05 (m, 3H),2.57 (m, 1H), 2.88 (m, 1H), 3.55 (m, 4H), 3.83 (m, 1H), 5.87 (d, J=6.0Hz, 1H), 5.97 (m, 1H), 7.73 (d, J=6.0 Hz, 1H);

MS (m/z): 332 (M+H)⁺, 276, 166.5 (M+2H)²⁺; HPLC retention time (min):2.98; HPLC condition: A.

Example 10(5)4-(perhydroazepin-1-yl)-2-[(3S)-1-(2-ethylbutyl)piperidin-3-ylamino]pyrimidineoil;

TLC: Rf 0.60 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CDCl₃): δ 0.84 (t, J=7.5 Hz, 6H), 1.31 (m, 5H), 1.54 (m, 5H), 1.75(m, 5H), 1.88 (m, 2H), 2.10 (d, J=7.0 Hz, 2H), 2.31 (m, 3H), 2.65 (m,1H), 3.56 (m, 4H), 4.02 (m, 1H), 5.17 (m, 1H), 5.76 (d, J=6.0 Hz, 1H),7.80 (d, J=6.0 Hz, 1H).

MS (m/z): 360 (M+H)⁺, 276, 180.5 (M+2H)²⁺;

HPLC retention time (min): 3.11; HPLC condition: A.

Example 10(6)4-(perhydroazepin-1-yl)-2-[(3S)-1-(2-pyridinylmethyl)piperidin-3-ylamino]pyrimidine

TLC: Rf 0.35 (ethyl acetate:methanol:triethylamine=20:2:1);

NMR (DMSO-d₆, 323K): δ 1.34 (m, 1H), 1.45 (m, 4H), 1.54 (m, 1H), 1.65(m, 5H), 1.77 (m, 1H), 1.99 (m, 1H), 2.13 (m, 1H), 2.65 (m, 1H), 2.89(m, 1H), 3.50 (m, 4H), 3.55 (d, J=13.5 Hz, 1H), 3.63 (d, J=13.5 Hz, 1H),3.86 (m, 1H), 5.84 (d, J=6.0 Hz, 1H), 5.99 (m, 1H), 7.23 (m, 1H), 7.44(d, J=8.0 Hz, 1H), 7.71 (d, J=6.0 Hz, 1H), 7.74 (dd, J=8.0, 2.0 Hz, 1H),8.47 (m, 1H);

MS (m/z): 367 (M+H)⁺, 184 (M+2H)²⁺;

HPLC retention time (min): 2.92; HPLC condition: A.

Example 10(7)4-(perhydroazepin-1-yl)-2-[(3S)-(1-cyclohexyl)piperidin-3-ylamino]pyrimidineoil;

TLC: Rf 0.48 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CDCl₃): δ 1.06 (m, 1H), 1.22 (m, 4H), 1.55 (m, 5H), 1.76 (m, 12H),2.28 (m, 2H), 2.45 (m, 1H), 2.56 (m, 1H), 2.95 (m, 1H), 3.57 (m, 4H),3.98 (m, 1H), 5.06 (m, 1H), 5.75 (d, J=6.0 Hz, 1H), 7.79 (d, J=6.0 Hz,1H).

MS (m/z): 358 (M+H)⁺, 276, 179.5 (M+2H)²⁺;

HPLC retention time (min): 2.94; HPLC condition: A.

Example 10(8)4-(perhydroazepin-1-yl)-2-[(3S)-1-(tetrahydro-2H-pyran-4-yl)piperidin-3-ylamino]pyrimidineoil;

TLC: Rf 0.45 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (CDCl₃): δ 1.55 (m, 8H), 1.75 (m, 8H), 1.91 (m, 1H), 2.28 (m, 1H),2.45 (m, 2H), 2.58 (m, 1H), 2.96 (m, 1H), 3.36 (m, 2H), 3.57 (m, 4H),4.01 (m, 2H), 5.11 (m, 1H), 5.77 (d, J=6.0 Hz, 1H), 7.79 (d, J=6.0 Hz,1H).

MS (m/z): 719 (2M+H)⁺, 360 (M+H)⁺, 276;

HPLC retention time (min): 2.78; HPLC condition: A.

Example 10(9)4-(perhydroazepin-1-yl)-2-[(3S)-(1-isobutyl)perhydroazepin-3-ylamino]pyrimidine

TLC: Rf 0.50 (ethyl acetate:methanol:triethylamine=20:2:1);

NMR (DMSO-d₆, 323K): δ 0.87 (d, J=6.5 Hz, 3H), 0.88 (d, J=6.5 Hz, 3H),1.48 (m, 4H), 1.62 (m, 5H), 1.68 (m, 4H), 1.76 (m, 2H), 2.21 (dd,J=12.0, 7.5 Hz, 1H), 2.26 (dd, J=12.0, 7.0 Hz, 1H), 2.60 (m, 3H), 2.77(dd, J=13.5, 4.0 Hz, 1H), 3.55 (m, 4H), 3.94 (m, 1H), 5.84 (d, J=6.0 Hz,1H), 5.87 (m, 1H), 7.72 (d, J=6.0 Hz, 1H);

MS (m/z): 346 (M+H)⁺, 290, 173.5 (M+2H)²⁺;

HPLC retention time (min): 3.00; HPLC condition: A.

Example 10(10)4-(perhydroazepin-1-yl)-2-[(3S)-1-(2-ethylbutyl)perhydroazepin-3-ylamino]pyrimidine

TLC: Rf 0.60 (chloroform:methanol:28% ammonia water=80:10:1);

NMR (DMSO-d₆, 323K): δ 0.83 (t, J=7.5 Hz, 3H), 0.85 (t, J=7.5 Hz, 3H),1.30 (m, 6H), 1.48 (m, 4H), 1.62 (m, 3H), 1.69 (m, 4H), 1.75 (m, 2H),2.29 (m, 2H), 2.58 (m, 3H), 2.76 (dd, J=13.5, 4.0 Hz, 1H), 3.55 (m, 4H),3.95 (m, 1H), 5.84 (m, 2H), 7.72 (d, J=6.0 Hz, 1H);

MS (m/z): 374 (M+H)⁺, 290, 187.5 (M+2H)²⁺;

HPLC retention time (min): 3.12; HPLC condition: A.

Example 10(11)4-(perhydroazepin-1-yl)-2-[(3S)-(1-cyclohexyl)pyrrolidin-3-ylamino]pyrimidineoil;

TLC: Rf 0.35 (ethyl acetate:methanol:triethylamine=20:2:1);

NMR (DMSO-d₆): δ 1.15 (m, 6H), 1.44 (m, 6H), 1.66 (m, 7H), 1.78 (m, 1H),2.01 (m, 2H), 2.34 (dd, J=9.0, 5.5 Hz, 1H), 2.55 (m, 1H), 2.87 (t, J=8.5Hz, 1H), 3.52 (m, 4H), 4.17 (m, 1H), 5.83 (d, J=6.0 Hz, 1H), 6.38 (m,1H), 7.71 (d, J=6.0 Hz, 1H);

MS (m/z): 344 (M+H)⁺, 262, 182;

HPLC retention time (min): 3.05; HPLC condition: A.

Example 11-0001 to Example 11-1035

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 11-0001N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N³,N³-dimethylpropane-1,3-diamine

NMR (DMSO-d₆): δ 1.63 (m, 2H), 2.11 (s, 6H), 2.23 (t, J=7.0 Hz, 2H),2.83 (t, J=6.0 Hz, 2H), 3.23 (q, J=6.5 Hz, 2H), 3.76 (t, J=6.0 Hz, 2H),4.66 (s, 2H), 6.04 (d, J=6.0 Hz, 1H), 6.53 (m, 1H), 7.19 (m, 4H), 7.80(d, J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 312 (M+H)⁺, 278, 156;

TLC: Rf 0.19 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0002N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 2.16 (s, 6H), 2.36 (t, J=6.9 Hz, 2H), 2.84 (t, J=5.7Hz, 2H), 3.32 (m, 2H), 3.76 (t, J=5.7 Hz, 2H), 4.67 (s, 2H), 6.06 (d,J=6.0 Hz, 1H), 6.28 (m, 1H), 7.17 (m, 4H) 7.80 (d, J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 298 (M+H)⁺, 149;

TLC: Rf 0.34 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0003 N-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethylacetamide

NMR (DMSO-d₆, 373.1K): δ 1.51 (m, 4H), 1.70 (m, 4H), 1.80 (s, 3H), 3.22(m, 2H), 3.32 (m, 2H), 3.56 (t, J=6.0 Hz, 4H), 5.85 (d, J=6.0 Hz, 1H),5.97 (m, 1H), 7.52 (m, 1H), 7.73 (d, J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 278 (M+H)⁺;

TLC: Rf 0.44 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0004(1R*,2R*)-N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]cyclohexane-1,2-diamine

NMR (DMSO-d₆): δ 1.15 (m, 4H), 1.66 (m, 2H), 1.82 (m, 1H), 1.97 (m, 1H),2.84 (t, J=6.0 Hz, 2H), 3.37 (m, 2H), 3.76 (t, J=6.0 Hz, 2H), 4.67 (s,2H), 6.05 (d, J=6.0 Hz, 1H), 6.35 (m, 1H), 7.17 (m, 4H), 7.80 (d, J=6.0Hz, 1H);

MS (MALDI-TOF, Pos.): 324 (M+H)⁺;

TLC: Rf 0.41 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0005(1S*,2R*)-N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]cyclohexane-1,2-diamine

NMR (DMSO-d₆): δ 1.27 (m, 2H), 1.51 (m, 6H), 2.83 (t, J=6.0 Hz, 2H),2.98 (m, 1H), 3.77 (m, 3H), 4.66 (s, 2H), 6.04 (m, 2H), 7.18 (m, 4H),7.80 (d, J=6.0 Hz, 1H);

MS (MALDI-TOF, Pos.): 324 (M+H)⁺;

TLC: Rf 0.36 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0006 3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepane-2-one

NMR (DMSO-d₆, 373K): δ 1.32 (m, 2H), 1.49 (m, 4H), 1.72 (m, 6H), 1.92(m, 1H), 2.08 (m, 1H), 3.18 (m, 2H), 3.57 (m, 4H), 4.44 (m, 1H), 5.88(m, 2H), 7.47 (m, 1H), 7.76 (d, J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 607 (2M+H)⁺, 304 (M+H)⁺;

TLC: Rf 0.50 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0007(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1,3′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.25 (m, 3H), 1.44 (m, 5H), 1.68 (m, 8H), 2.02 (m, 1H),2.38 (m, 4H), 2.65 (m, 1H), 2.81 (d, J=12.30 Hz, 1H), 2.98 (m, 2H), 3.52(m, 4H), 3.77 (m, 2H), 5.83 (d, J=6.0 Hz, 1H), 6.10 (m, 1H), 7.70 (d,J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 359 (M+H)⁺, 276;

TLC: Rf 0.21 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0008(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.29 (m, 3H), 1.46 (m, 5H), 1.70 (m, 8H), 1.95 (m, 1H),2.16 (m, 1H), 2.30 (m, 1H), 2.42 (m, 2H), 2.64 (m, 1H), 2.97 (m, 3H),3.52 (m, 4H), 3.78 (m, 2H), 5.83 (d, J=6.0 Hz, 1H), 6.12 (m, 1H), 7.70(d, J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 359 (M+H)⁺, 276, 180 (M+2H)²⁺;

TLC: Rf 0.18 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00092-[4-((1S*,2S*)-2-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]aminocyclohexyl)piperazin-1-yl]ethanol

NMR (DMSO-d₆): δ 1.22 (m, 4H), 1.74 (m, 4H), 2.26 (m, 6H), 2.40 (m, 2H),2.66 (m, 2H), 3.05 (m, 2H), 3.35 (m, 2H), 3.84 (m, 3H), 4.32 (m, 1H),4.76 (s, 2H), 6.23 (m, 1H), 7.07 (t, J=7.3 Hz, 1H), 7.19 (m, 4H), 7.32(d, J=8.2 Hz, 1H), 7.51 (t, J=7.30 Hz, 1H), 7.81 (d, J=8.2 Hz, 1H);

MS (ESI, Pos. 20 V): 487 (M+H)⁺, 244;

TLC: Rf 0.47 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00104-azepan-1-yl-N-[(1-ethylpyrrolidin-2-yl)methyl]pyrimidin-2-amine

NMR (CDCl₃): δ 1.24 (t, J=7.10 Hz, 3H), 1.54 (m, 4H), 1.75 (m, 4H), 1.80(m, 2H), 2.01 (m, 2H), 2.50 (m, 2H), 3.07 (m, 1H), 3.56 (m, 8H), 5.83(d, J=6.30 Hz, 1H), 6.16 (m, 1H), 7.72 (d, J=6.30 Hz, 1H);

MS (ESI, Pos. 20 V): 304 (M+H)⁺;

TLC: Rf 0.33 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0011N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²,N²-diisopropylethane-1,2-diamine

NMR (CDCl₃): δ 1.10 (d, J=6.6 Hz, 12H), 1.53 (m, 4H), 1.74 (m, 4H), 2.75(t, J=6.3 Hz, 2H), 3.14 (m, 2H), 3.46 (m, 2H), 3.57 (m, 4H), 5.79 (d,J=6.3 Hz, 1H), 5.90 (m, 1H), 7.73 (d, J=6.3 Hz, 1H);

MS (ESI, Pos. 20 V): 320 (M+H)⁺;

TLC: Rf 0.33 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00124-azepan-1-yl-N-(3-pyrrolidin-1-ylpropyl)pyrimidin-2-amine

NMR (CDCl₃): δ 1.52 (m, 4H), 1.74 (m, 4H), 1.83 (m, 4H), 2.60 (m, 6H),2.92 (m, 2H), 3.42 (t, J=6.6 Hz, 2H), 3.54 (m, 4H), 5.25 (m, 1H), 5.76(d, J=6.3 Hz, 1H), 7.76 (d, J=6.3 Hz, 1H);

MS (ESI, Pos. 20 V): 304 (M+H)⁺;

TLC: Rf 0.35 (CHCl₃:MeOH=9:1).

Example 11-00134-azepan-1-yl-N-(3-morpholin-4-ylpropyl)pyrimidin-2-amine

NMR (CDCl₃): δ 1.49 (m, 4H), 1.70 (m, 6H), 2.37 (m, 6H), 3.37 (q, J=6.60Hz, 2H), 3.54 (m, 4H), 3.64 (t, J=4.70 Hz, 4H), 4.82 (m, 1H), 5.77 (d,J=6.60 Hz, 1H), 7.59 (d, J=6.60 Hz, 1H);

MS (ESI, Pos. 20 V): 320 (M+H)⁺, 233;

TLC: Rf 0.33 (CHCl₃:MeOH=9:1).

Example 11-0014 1-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]propyl di -2-

NMR(CDCl₃): δ 1.53 (m, 4H), 1.76 (m, 4H), 1.80 (m, 2H), 1.99 (m, 2H),2.35 (t, J=7.90 Hz, 2H), 3.36 (m, 4H), 3.63 (m, 6H), 5.82 (d, J=6.60 Hz,1H), 6.39 (m, 1H), 7.65 (d, J=6.60 Hz, 1H);

MS (ESI, Pos. 20 V): 318 (M+H)⁺;

TLC: Rf 0.50 (CHCl₃:MeOH=9:1).

Example 11-00154-azepan-1-yl-N-[3-(4-methylpiperazin-1-yl)propyl]pyrimidin-2-amine

NMR (CDCl₃): δ 1.53 (m, 4H), 1.75 (m, 6H), 2.27 (s, 3H), 2.45 (m, 8H),2.64 (m, 2H), 3.40 (m, 2H), 3.55 (m, 4H), 5.48 (m, 1H), 5.77 (d, J=6.30Hz, 1H), 7.76 (d, J=6.30 Hz, 1H);

MS (ESI, Pos. 20 V): 333 (M+H)⁺, 233;

TLC: Rf 0.25 (CHCl₃:MeOH=9:1).

Example 11-00164-azepan-1-yl-N-[(3S)-1-cyclopentylpiperidin-3-yl]pyrimidin-2-amine

NMR (CDCl₃): δ 1.41 (m, 2H), 1.52 (m, 6H), 1.65 (m, 2H), 1.79 (m, 8H),1.96 (m, 2H), 2.06 (m, 1H), 2.22 (m, 1H), 2.51 (m, 1H), 2.63 (m, 1H),3.00 (m, 1H), 3.56 (m, 4H), 4.02 (m, 1H), 5.01 (m, 1H), 5.76 (d, J=6.20Hz, 1H), 7.78 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 344 (M+H)⁺, 247, 172.5 (M+2H)²⁺;

TLC: Rf 0.60 (AcOEt:MeOH:TEA=20:10:1).

Example 11-0017N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-phenylethane-1,2-diamine

NMR (CDCl₃): δ 1.55 (s, 4H), 1.76 (m, 4H), 3.35 (t, J=5.70 Hz, 2H), 3.60(m, 4H), 3.64 (q, J=5.70 Hz, 2H), 4.29 (m, 1H), 5.27 (m, 1H), 5.82 (d,J=6.30 Hz, 1H), 6.63 (m, 3H), 7.15 (dd, J=8.50, 7.10 Hz, 2H), 7.79 (d,J=6.30 Hz, 1H);

MS (ESI, Pos. 20 V): 312 (M+H)⁺;

TLC: Rf 0.45 (CHCl₃:MeOH=9:1).

Example 11-0018 1-[2-(3-phenylimidazolidin-1-yl)pyrimidin-4-yl]azepane

NMR (CDCl₃): δ 1.54 (m, 4H), 1.77 (m, 4H), 3.58 (t, J=6.80 Hz, 2H), 3.59(m, 4H), 3.92 (t, J=6.60 Hz, 2H), 4.87 (s, 2H), 5.85 (d, J=6.00 Hz, 1H),6.69 (d, J=8.50 Hz, 2H), 6.79 (t, J=7.10 Hz, 1H), 7.27 (dd, J=8.50, 7.10Hz, 2H), 7.91 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 324 (M+H)⁺;

TLC: Rf 0.35 (AcOEt:hexane=1:2).

Example 11-0019N-[4-(2,3-dihydro-1H-indol-1-yl)pyrimidin-2-yl]ethane-1,2-diaminedihydrochloride

NMR (300 MHz, CD₃OD): δ 8.42 (brd, J=8.1 Hz, 1H), 7.92 (d, J=7.2 Hz,1H), 7.45-7.27 (m, 2H), 7.18 (m, 1H), 6.51 (d, J=7.2 Hz, 1H), 4.26 (t,J=8.1 Hz, 2H), 3.94-3.78 (m, 2H), 3.50-3.25 (m, 4H);

MS (FAB, Pos., Glycerin+m-NBA): 256 (M+H)⁺, 239, 213;

TLC: Rf 0.13 (n-BuOH:AcOH:H₂O=4:2:1).

Example 11-0020N-[4-(3,4-dihydroquinolin-1(2H)-yl)pyrimidin-2-yl]ethane-1,2-diaminedihydrochloride

NMR (300 MHz, CD₃OD): δ 7.72 (brd, J=7.2 Hz, 1H), 7.48-7.22 (m, 4H),6.64 (d, J=7.2 Hz, 1H), 4.20-4.00 (m, 2H), 3.94-3.70 (m, 2H), 3.36-3.18(m, 2H), 2.79 (t, J=6.6 Hz, 2H), 2.12-2.00 (m, 2H);

MS (FAB, Pos., Glycerin+m-NBA): 270 (M+H)⁺, 253, 227;

TLC: Rf 0.22 (n-BuOH:AcOH:H₂O=4:2:1).

Example 11-0021 4-azepan-1-yl-N-(pyridin-2-ylmethyl)pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.34 (m, 4H), 1.63 (m, 4H), 3.52 (m, 4H), 4.48 (d,J=5.90 Hz, 2H), 5.86 (d, J=5.90 Hz, 1H), 6.97 (m, 1H), 7.17 (m, 1H),7.24 (d, J=7.70 Hz, 1H), 7.67 (td, J=7.70, 1.80 Hz, 1H), 7.72 (d, J=5.90Hz, 1H), 8.45 (m, 1H);

MS (ESI, Pos. 20 V): 284 (M+H)⁺;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0022N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-(pyridin-2-ylmethyl)ethane-1,2-diamine

NMR (CD₃OD): δ 1.52 (m, 4H), 1.74 (m, 4H), 2.83 (t, J=6.20 Hz, 2H), 3.47(t, J=6.20 Hz, 2H), 3.53 (m, 4H), 3.90 (s, 2H), 5.91 (d, J=6.20 Hz, 1H),7.27 (m, 1H), 7.44 (m, 1H), 7.66 (d, J=6.20 Hz, 1H), 7.76 (m, 1H), 8.46(m, 1H);

MS (ESI, Pos. 20 V): 327 (M+H)⁺;

TLC: Rf 0.50 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0023 N-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethylguanidinedihydrochloride

NMR (DMSO-d₆): δ 1.46 (m, 4H), 1.71 (m, 4H), 3.35 (m, 2H), 3.47 (m, 2H),3.63 (m, 2H), 3.79 (t, J=6.00 Hz, 2H), 6.40 (d, J=7.30 Hz, 1H), 7.34 (m,4H), 7.83 (d, J=7.30 Hz, 1H), 7.99 (m, 1H), 8.21 (m, 1H), 12.63 (m, 1H);

MS (ESI, Pos. 20 V): 555 (2M+H)⁺, 278 (M+H)⁺, 261;

TLC: Rf 0.26 (AcOEt:AcOH:H₂O=3:1:1).

Example 11-00242-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N,N,N-trimethylethanaminiumiodide

NMR (DMSO-d₆): δ 1.46 (m, 4H), 1.69 (m, 4H), 3.11 (s, 9H), 3.41 (m, 2H),3.51 (m, 4H), 3.68 (m, 2H), 5.94 (d, J=6.00 Hz, 1H), 6.72 (m, 1H), 7.77(d, J=6.00 Hz, 1H);

MS (MALDI-TOF, Pos.): 278 (M⁺), 233, 219;

TLC: Rf 0.10 (AcOEt:AcOH:H₂O=3:1:1).

Example 11-0025N-[4-(3,6-dihydropyridin-1(2H)-yl)pyrimidin-2-yl]ethane-1,2-diaminedihydrochloride

NMR (DMSO-d₆): δ 2.19 (m, 2H), 2.98 (m, 2H), 3.64 (m, 2H), 3.77 (m, 1H),3.98 (m, 1H), 4.12 (m, 1H), 4.34 (m, 1H), 5.77 (d, J=7.30 Hz, 1H), 5.94(m, 1H), 6.58 (m, 1H), 7.88 (d, J=7.30 Hz, 1H), 8.40 (m, 4H), 12.64 (m,1H);

MS (MALDI-TOF, Pos.): 220 (M+H)⁺;

TLC: Rf 0.49 (CHCl₃:MeOH:NH₄OH=80:20:4).

Example 11-0026N-[4-(1,4′-bipiperidin-1′-yl)pyrimidin-2-yl]ethane-1,2-diaminetrihydrochloride

NMR (DMSO-d₆): δ 1.39 (m, 1H), 1.73 (m, 5H), 1.95 (m, 2H), 2.26 (m, 2H),2.93 (m, 5H), 3.18 (m, 1H), 3.38 (m, 2H), 3.46 (m, 1H), 3.64 (q, J=6.00Hz, 2H), 4.35 (m, 2H), 5.10 (m, 1H), 6.61 (d, J=7.30 Hz, 1H), 7.90 (d,J=7.30 Hz, 1H), 8.28 (m, 3H), 11.04 (m, 1H), 12.68 (m, 1H);

MS (MALDI-TOF, Pos.): 305 (M+H)⁺;

TLC: Rf 0.39 (CHCl₃:MeOH:NH₄OH=80:20:4).

Example 11-0027 N-(4-piperidin-1-ylpyrimidin-2-yl)ethane-1,2-diamine

NMR (DMSO-d₆): δ 1.44 (m, 4H), 1.63 (m, 2H), 2.91 (t, J=6.00 Hz, 2H),3.41 (m, 2H), 3.52 (m, 4H), 6.06 (d, J=5.90 Hz, 1H), 6.59 (m, 1H), 7.80(m, 3H);

MS (LC-MS, APCI, Pos. 20 V): 222 (M+H)⁺, 179;

TLC: Rf 0.48 (CHCl₃:MeOH:NH₄OH=80:20:4).

Example 11-0028N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-isopropylethane-1,2-diamine

NMR (DMSO-d₆): δ 0.94 (d, J=6.20 Hz, 6H), 1.42 (m, 4H), 1.67 (m, 4H),2.62 (m, 2H), 2.68 (m, 1H), 3.24 (m, 2H), 3.62 (m, 4H), 5.83 (d, J=6.00Hz, 1H), 6.26 (m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 555 (2M+H)⁺, 278 (M+H)⁺;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=80:20:4).

Example 11-00294-azepan-1-yl-N-(1-isopropylpyrrolidin-3-yl)pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.98 (m, 6H), 1.45 (m, 5H), 1.62 (m, 5H), 2.05 (m, 1H),2.30 (m, 2H), 2.54 (m, 1H), 2.84 (t, J=7.90 Hz, 1H), 3.60 (m, 4H), 4.16(m, 1H), 5.83 (d, J=5.90 Hz, 1H), 6.39 (m, 1H), 7.71 (d, J=5.90 Hz, 1H);

MS (ESI, Pos. 20 V): 304 (M+H)⁺, 262;

TLC: Rf 0.19 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00304-azepan-1-yl-N-[1-(1-ethylpropyl)pyrrolidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.80 (m, 6H), 1.33 (m, 4H), 1.47 (m, 5H), 1.64 (m, 4H),2.03 (m, 2H), 2.30 (dd, J=9.00, 5.70 Hz, 1H), 2.55 (m, 2H), 2.88 (t,J=7.90 Hz, 1H), 3.60 (m, 4H), 4.17 (m, 1H), 5.83 (d, J=6.20 Hz, 1H),6.39 (m, 1H), 7.71 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 332 (M+H)⁺, 262, 193;

TLC: Rf 0.26 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00314-azepan-1-yl-N-(1-cyclohexylpyrrolidin-3-yl)pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.15 (m, 5H), 1.47 (m, 5H), 1.60 (m, 7H), 1.79 (m, 2H),2.02 (m, 2H), 2.32 (dd, J=9.20, 5.50 Hz, 1H), 2.55 (m, 2H), 2.86 (t,J=8.10 Hz, 1H), 3.59 (m, 4H), 4.17 (m, 1H), 5.83 (d, J=6.20 Hz, 1H),6.38 (m, 1H), 7.71 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 344 (M+H)⁺, 262;

TLC: Rf 0.26 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00324-azepan-1-yl-N-[(3R)-1-benzylpyrrolidin-3-yl]pyrimidin-2-amine

NMR (CDCl₃): δ 1.53 (m, 4H), 1.73 (m, 5H), 2.31 (m, 1H), 2.49 (m, 2H),2.70 (m, 1H), 2.90 (m, 1H), 3.55 (m, 4H), 3.63 (s, 2H), 4.45 (m, 1H),5.44 (m, 1H), 5.79 (d, J=6.20 Hz, 1H), 7.30 (m, 5H), 7.74 (d, J=6.20 Hz,1H);

MS (ESI, Pos. 20 V): 352 (M+H)⁺, 262, 192;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00334-azepan-1-yl-N-[(3S)-1-benzylpyrrolidin-3-yl]pyrimidin-2-amine oil;

NMR (CDCl₃): δ 1.53 (m, 4H), 1.72 (m, 5H), 2.33 (m, 1H), 2.51 (m, 2H),2.70 (m, 1H), 2.90 (dd, J=9.50, 6.60 Hz, 1H), 3.58 (m, 4H), 3.63 (s,2H), 4.46 (m, 1H), 5.37 (m, 1H), 5.79 (d, J=6.20 Hz, 1H), 7.32 (m, 5H),7.75 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 352 (M+H)⁺, 262, 192;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00344-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]pyrimidin-2-amine

NMR (CDCl₃): δ 1.54 (m, 4H), 1.74 (m, 5H), 2.33 (m, 1H), 2.59 (m, 2H),2.78 (m, 1H), 2.96 (m, 1H), 3.57 (m, 4H), 3.76 (d, J=13.60 Hz, 1H), 3.82(d, J=13.60 Hz, 1H), 4.50 (m, 1H), 5.80 (d, J=6.20 Hz, 1H), 5.81 (m,1H), 7.15 (m, 1H), 7.43 (d, J=7.70 Hz, 1H), 7.65 (td, J=7.70, 1.80 Hz,1H), 7.72 (d, J=6.20 Hz, 1H), 8.54 (m, 1H);

MS (ESI, Pos. 20 V): 353 (M+H)⁺, 177 (M+2H)²⁺;

TLC: Rf 0.30 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00354-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)pyrrolidin-3-yl]pyrimidin-2-amine

NMR (CDCl₃): δ 0.86 (t, J=7.30 Hz, 6H), 1.36 (m, 5H), 1.54 (m, 4H), 1.75(m, 5H), 2.29 (m, 3H), 2.46 (m, 2H), 2.67 (m, 1H), 2.83 (m, 1H), 3.57(m, 4H), 4.45 (m, 1H), 5.26 (m, 1H), 5.79 (d, J=6.20 Hz, 1H), 7.78 (d,J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 346 (M+H)⁺, 289, 262;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00364-azepan-1-yl-N-[(3S)-1-(cyclohexylmethyl)pyrrolidin-3-yl]pyrimidin-2-amine

NMR (CDCl₃): δ 0.88 (m, 2H), 1.20 (m, 4H), 1.45 (m, 1H), 1.54 (m, 4H),1.75 (m, 9H), 2.27 (m, 3H), 2.47 (m, 2H), 2.68 (m, 1H), 2.87 (m, 1H),3.58 (m, 4H), 4.46 (m, 1H), 5.28 (m, 1H), 5.80 (d, J=6.20 Hz, 1H), 7.77(d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 358 (M+H)⁺, 262;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00374-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)pyrrolidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.81 (m, 6H), 1.26 (m, 6H), 1.45 (m, 4H), 1.63 (m, 4H),2.07 (m, 1H), 2.21 (m, 3H), 2.43 (m, 2H), 2.79 (m, 1H), 3.43 (m, 4H),4.19 (m, 1H), 5.84 (d, J=5.90 Hz, 1H), 6.40 (m, 1H), 7.71 (d, J=5.90 Hz,1H);

MS (ESI, Pos. 20 V): 346 (M+H)⁺, 262, 173.5 (M+2H)⁺;

TLC: Rf 0.28 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00384-azepan-1-yl-N-[(3R)-1-(cyclohexylmethyl)pyrrolidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.82 (m, 2H), 1.14 (m, 3H), 1.35 (m, 1H), 1.43 (m, 4H),1.65 (m, 10H), 2.05 (m, 1H), 2.15 (m, 2H), 2.24 (m, 1H), 2.40 (m, 2H),2.74 (m, 1H), 3.52 (m, 4H), 4.19 (m, 1H), 5.84 (d, J=5.90 Hz, 1H), 6.45(m, 1H), 7.71 (d, J=5.90 Hz, 1H);

MS (ESI, Pos. 20 V): 358 (M+H)⁺, 179.5 (M+2H)⁺;

TLC: Rf 0.37 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00404-azepan-1-yl-N-(1-tetrahydro-2H-pyran-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.28 (m, 2H), 1.47 (m, 4H), 1.69 (m, 6H), 2.07 (m, 2H),2.33 (m, 1H), 2.61 (m, 1H), 2.86 (m, 1H), 3.31 (m, 4H), 3.39 (m, 4H),3.84 (m, 2H), 4.21 (m, 1H), 5.84 (d, J=5.90 Hz, 1H), 6.39 (m, 1H), 7.71(d, J=5.90 Hz, 1H);

MS (ESI, Pos. 20 V): 346 (M+H)⁺, 290;

TLC: Rf 0.44 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00414-azepan-1-yl-N-[(3R)-1-cyclohexylpyrrolidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.16 (m, 5H), 1.50 (m, 5H), 1.67 (m, 7H), 1.83 (m, 2H),2.07 (m, 3H), 2.70 (m, 2H), 2.98 (m, 1H), 3.63 (m, 4H), 4.22 (m, 1H),5.86 (d, J=5.90 Hz, 1H), 6.43 (m, 1H), 7.72 (d, J=5.90 Hz, 1H);

MS (ESI, Pos. 20 V): 344 (M+H)⁺, 262;

TLC: Rf 0.39 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0042 4-azepan-1-yl-N-[(3S)-pyrrolidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.42 (m, 4H), 1.67 (m, 5H), 1.93 (m, 1H), 2.66 (dd,J=11.10, 4.50 Hz, 1H), 2.76 (m, 1H), 2.94 (m, 2H), 3.81 (m, 4H), 4.23(m, 1H), 5.85 (d, J=6.00 Hz, 1H), 6.48 (m, 1H), 7.72 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 262 (M+H)⁺, 131.5 (M+2H)²⁺;

TLC: Rf 0.20 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0043(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-cyclohexylazepan-3-amine

NMR (DMSO-d₆): δ 1.18 (m, 4H), 1.40 (m, 5H), 1.56 (m, 5H), 1.72 (m, 8H),2.33 (m, 2H), 2.69 (m, 5H), 3.57 (m, 4H), 3.86 (m, 1H), 5.81 (d, J=6.20Hz, 1H), 5.95 (m, 1H), 7.70 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 290, 186.5 (M+2H)²⁺;

TLC: Rf 0.47 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0044(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-tetrahydro-2H-pyran-4-ylazepan-3-amine

NMR (DMSO-d₆): δ 1.37 (m, 7H), 1.68 (m, 11H), 2.70 (m, 5H), 3.17 (m,2H), 3.55 (m, 4H), 3.85 (m, 3H), 5.82 (d, J=6.00 Hz, 1H), 6.01 (m, 1H),7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 374 (M+H)⁺, 316, 290, 187.5 (M+2H)²⁺;

TLC: Rf 0.50 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0045 4-azepan-1-yl-N-cycloheptylpyrimidin-2-amine

NMR (DMSO-d₆): δ 1.46 (m, 12H), 1.69 (m, 6H), 1.85 (m, 2H), 3.52 (m,4H), 3.77 (m, 1H), 5.80 (d, J=6.00 Hz, 1H), 6.26 (m, 1H), 7.70 (d,J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 577 (2M+H)⁺, 289 (M+H)⁺;

TLC: Rf 0.41 (CHCl₃:MeOH=10:1).

Example 11-0046(3S)-1′-acetyl-N-(4-azepan-1-ylpyrimidin-2-yl)-1,3′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.30 (m, 8H), 1.71 (m, 8H), 1.94 (m, 3H), 2.04 (m, 1H),2.24 (m, 2H), 2.48 (m, 1H), 2.69 (m, 1H), 2.96 (m, 2H), 3.48 (m, 4H),3.76 (m, 2H), 4.33 (m, 1H), 5.84 (d, J=6.00 Hz, 1H), 6.19 (m, 1H), 7.71(d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 401 (M+H)⁺, 276, 201 (M+2H)²⁺;

TLC: Rf 0.52 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0047(3S)-1′-acetyl-N-(4-azepan-1-ylpyrimidin-2-yl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.22 (m, 3H), 1.46 (m, 5H), 1.71 (m, 8H), 1.95 (s, 3H),2.02 (m, 1H), 2.21 (m, 1H), 2.42 (m, 2H), 2.66 (m, 1H), 2.96 (m, 2H),3.52 (m, 4H), 3.80 (m, 2H), 4.38 (m, 1H), 5.83 (d, J=6.00 Hz, 1H), 6.09(m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 401 (M+H)⁺, 201 (M+2H)²⁺;

TLC: Rf 0.46 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0048(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(methylsulfonyl)-1,3′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.28 (m, 3H), 1.47 (m, 5H), 1.64 (m, 5H), 1.82 (m, 3H),2.04 (m, 1H), 2.25 (m, 1H), 2.48 (m, 4H), 2.71 (m, 1H), 2.82 (s, 3H),2.98 (m, 1H), 3.50 (m, 5H), 3.78 (m, 1H), 5.84 (d, J=6.00 Hz, 1H), 6.14(m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 437 (M+H)⁺, 276, 219 (M+2H)²⁺;

TLC: Rf 0.54 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0049(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(methylsulfonyl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.27 (m, 3H), 1.44 (m, 6H), 1.63 (m, 5H), 1.79 (m, 3H),1.99 (m, 1H), 2.18 (m, 1H), 2.35 (t, J=11.10 Hz, 1H), 2.67 (t, J=11.10Hz, 3H), 2.82 (s, 3H), 2.98 (m, 1H), 3.52 (m, 5H), 3.80 (m, 1H), 5.83(d, J=6.00 Hz, 1H), 6.09 (m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 873 (2M+H)⁺, 437 (M+H)⁺, 219 (M+2H)²⁺;

TLC: Rf 0.63 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00501-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanecarbonitrile

NMR (DMSO-d₆): δ 1.29 (m, 3H), 1.47 (m, 6H), 1.69 (m, 9H), 1.88 (m, 1H),2.07 (m, 3H), 2.90 (m, 1H), 3.15 (m, 3H), 3.53 (m, 4H), 3.83 (m, 1H),5.84 (d, J=6.00 Hz, 1H), 6.25 (m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 765 (2M+H)⁺, 383 (M+H)⁺, 356, 276;

TLC: Rf 0.26 (AcOEt).

Example 11-00514-azepan-1-yl-N-[(3S)-1-(1-methylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.77 (s, 3H), 1.18 (m, 6H), 1.44 (m, 7H), 1.67 (m, 9H),1.88 (m, 1H), 2.07 (m, 1H), 2.70 (m, 1H), 2.99 (m, 1H), 3.53 (m, 4H),3.81 (m, 1H), 5.82 (d, J=5.90 Hz, 1H), 6.08 (m, 1H), 7.70 (d, J=5.90 Hz,1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 276;

TLC: Rf 0.67 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00524-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanone

NMR (DMSO-d₆): δ 1.41 (m, 6H), 1.63 (m, 5H), 1.83 (m, 4H), 2.00 (m, 1H),2.22 (m, 2H), 2.38 (m, 3H), 2.96 (m, 4H), 3.60 (m, 4H), 3.98 (m, 1H),6.05 (m, 1H), 6.98 (m, 1H), 7.76 (d, J=6.60 Hz, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 290, 186.5 (M+2H)²⁺;

TLC: Rf 0.67 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00534-azepan-1-yl-N-[(3S)-1-(3-methylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆, 373 K): δ 0.88 (m, 3H), 1.16 (m, 1H), 1.27 (m, 1H), 1.38(m, 4H), 1.50 (m, 8H), 1.63 (m, 2H), 1.70 (m, 4H), 1.92 (m, 1H), 2.09(m, 1H), 2.22 (m, 1H), 2.36 (m, 1H), 2.59 (m, 1H), 2.89 (m, 1H), 3.55(t, J=6.00 Hz, 4H), 3.83 (m, 1H), 5.54 (d, J=8.40 Hz, 1H), 5.83 (d,J=6.00 Hz, 1H), 7.72 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 276, 186.5 (M+2H)²⁺;

TLC: Rf 0.42 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00544-azepan-1-yl-N-[(3S)-1-(3,5-dimethylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.53 (m, 2H), 0.80 (m, 6H), 1.45 (m, 8H), 1.65 (m, 8H),1.83 (m, 2H), 2.17 (m, 1H), 2.48 (m, 2H), 2.70 (m, 1H), 2.93 (m, 1H),3.50 (m, 4H), 3.77 (m, 1H), 5.82 (d, J=6.00 Hz, 1H), 6.03 (m, 1H), 7.70(d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 386 (M+H)⁺, 276, 193.5 (M+2H)²⁺;

TLC: Rf 0.47 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00554-azepan-1-yl-N-[(3S)-1-(3,4-dimethylcyclopentyl)piperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.86 (m, 6H), 1.05 (m, 2H), 1.29 (m, 4H), 1.45 (m, 4H),1.66 (m, 8H), 1.89 (m, 2H), 2.58 (m, 2H), 2.96 (m, 1H), 3.49 (m, 4H),3.73 (m, 1H), 5.82 (d, J=6.00 Hz, 1H) 6.06 (m, 1H), 7.70 (d, J=6.00 Hz,1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 276, 186.5 (M+2H)²⁺;

TLC: Rf 0.42 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00564-azepan-1-yl-N-[(3S)-1-cycloheptylpiperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.44 (m, 14H), 1.66 (m, 10H), 1.97 (m, 1H), 2.18 (m,1H), 2.45 (m, 2H), 2.86 (m, 1H), 3.51 (m, 4H), 3.71 (m, 1H), 5.82 (d,J=6.00 Hz, 1H), 6.00 (m, 1H), 7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 276, 186.5 (M+2H)²⁺;

TLC: Rf 0.42 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00574-azepan-1-yl-N-[(3S)-1-(3,5-dimethylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.47 (m, 2H), 0.81 (m, 6H), 1.45 (m, 6H), 1.67 (m,10H), 2.04 (m, 1H), 2.21 (m, 1H), 2.36 (m, 1H), 2.58 (m, 1H), 2.90 (m,1H), 3.50 (m, 4H), 4.17 (m, 1H), 5.83 (d, J=6.00 Hz, 1H), 6.35 (m, 1H),7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 262;

TLC: Rf 0.42 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00584-azepan-1-yl-N-[(3S)-1-ethylpiperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.96 (t, J=7.00 Hz, 3H), 1.28 (m, 1H), 1.44 (m, 5H),1.66 (m, 6H), 1.91 (m, 1H), 2.28 (m, 2H), 2.48 (m, 1H), 2.58 (m, 1H),2.89 (m, 1H), 3.51 (m, 4H), 3.77 (m, 1H) 5.83 (d, J=5.90 Hz, 1H), 6.05(m, 1H), 7.71 (d, J=5.90 Hz, 1H);

MS (ESI, Pos. 20 V): 304 (M+H)⁺, 152.5 (M+2H)²⁺;

TLC: Rf 0.40 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00594-azepan-1-yl-N-[1-(1-ethylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.75 (t, J=7.50 Hz, 3H), 1.30 (m, 9H), 1.45 (m, 6H),1.69 (m, 9H), 1.96 (m, 1H), 2.16 (m, 1H), 2.73 (m, 1H), 2.99 (m, 1H),3.50 (m, 4H), 3.74 (m, 1H), 5.81 (d, J=6.00 Hz, 1H), 6.04 (m, 1H), 7.69(d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 386 (M+H)⁺, 276, 111;

TLC: Rf 0.38 (CHCl₃:MeOH=10:1).

Example 11-00604-azepan-1-yl-N-[1-(1-phenylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.04 (m, 1H), 1.29 (m, 5H), 1.46 (m, 5H), 1.65 (m, 9H),1.87 (m, 2H), 2.12 (m, 2H), 2.69 (m, 1H), 2.98 (m, 1H), 3.50 (m, 4H),3.77 (m, 1H), 5.82 (d, J=6.00 Hz, 1H), 6.03 (m, 1H), 7.19 (m, 1H), 7.29(m, 4H), 7.69 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 434 (M+H)⁺, 276, 159;

TLC: Rf 0.38 (CHCl₃:MeOH=10:1).

Example 11-0061N-(1-cyclohexylpiperidin-3-yl)-4-(1,4-oxazepan-4-yl)pyrimidin-2-amine

NMR (CDCl₃): δ 1.02 (m, 1H), 1.20 (m, 2H), 1.50 (m, 3H), 1.78 (m, 8H),1.96 (m, 2H), 2.26 (m, 2H), 2.46 (m, 1H), 2.53 (m, 1H), 2.89 (m, 1H),3.68 (m, 4H), 3.76 (m, 4H), 3.95 (m, 1H), 5.10 (d, J=9.30 Hz, 1H), 5.76(d, J=6.00 Hz, 1H), 7.82 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 360 (M+H)⁺, 278, 180.5 (M+2H)⁺;

TLC: Rf 0.38 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0062N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopentylacetyl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.11 (m, 3H), 1.26 (m, 2H), 1.51 (m, 9H), 1.71 (m,10H), 1.93 (m, 1H), 2.06 (m, 1H), 2.18 (m, 1H), 2.27 (m, 2H), 2.41 (m,2H), 2.68 (m, 1H), 2.93 (m, 2H), 3.50 (m, 4H), 3.72 (m, 1H), 3.89 (m,1H), 4.43 (m, 1H), 5.83 (d, J=6.00 Hz, 1H), 6.10 (m, 1H), 7.70 (d,J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 469 (M+H)⁺, 359, 235 (M+2H)²⁺, 180;

TLC: Rf 0.66 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00633-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(tert-butyl)-1,4′-bipiperidin-1′-carboxamide

NMR (DMSO-d₆): δ 1.21 (s, 9H), 1.30 (m, 3H), 1.45 (m, 5H), 1.67 (m, 8H),1.96 (m, 1H), 2.15 (m, 1H), 2.37 (m, 3H), 2.68 (m, 1H), 2.96 (m, 1H),3.52 (m, 4H), 3.76 (m, 1H), 3.98 (m, 2H), 5.68 (s, 1H), 5.84 (d, J=6.00Hz, 1H), 6.13 (m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 458 (M+H)⁺, 276, 180;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0064 isopropyl3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidine-1′-carboxylate

NMR (DMSO-d₆): δ 1.15 (d, J=6.20 Hz, 6H), 1.27 (m, 3H), 1.45 (m, 5H),1.69 (m, 8H), 1.97 (m, 1H), 2.19 (m, 1H), 2.38 (m, 1H), 2.72 (m, 3H),3.00 (m, 1H), 3.50 (m, 4H), 3.74 (m, 1H), 3.99 (m, 2H), 4.74 (m, 1H),5.84 (d, J=6.20 Hz, 1H), 6.15 (m, 1H), 7.70 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 445 (M+H)⁺, 359, 276, 202;

TLC: Rf 0.57 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0065(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclohexylcarbonyl)-1,4′-bipiperidin-3-aminenoncrystalline material;

NMR (CDCl₃): δ 1.24 (m, 4H), 1.52 (m, 8H), 1.71 (m, 15H), 2.25 (m, 1H),2.47 (m, 4H), 2.95 (m, 2H), 3.55 (m, 4H), 3.96 (m, 2H), 4.64 (m, 1H),5.01 (m, 1H), 5.75 (d, J=6.00 Hz, 1H), 7.77 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 469 (M+H)⁺, 359, 318, 212, 111;

TLC: Rf 0.48 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0066(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopentylcarbonyl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.20 (m, 4H), 1.44 (m, 7H), 1.69 (m, 14H), 1.96 (m,1H), 2.20 (m, 1H), 2.40 (m, 1H), 2.68 (m, 1H), 2.96 (m, 3H), 3.51 (m,4H), 3.76 (m, 1H), 4.03 (m, 1H), 4.45 (m, 1H), 5.84 (d, J=6.00 Hz, 1H),6.16 (m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 455 (M+H)⁺, 359;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0067(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methylbutanoyl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 0.77 (t, J=7.40 Hz, 3H), 0.94 (m, 3H), 1.19 (m, 5H),1.46 (m, 6H), 1.71 (m, 8H), 1.97 (m, 1H), 2.20 (m, 1H), 2.39 (m, 1H),2.66 (m, 2H), 3.00 (m, 2H), 3.50 (m, 4H) 3.75 (m, 1H), 4.01 (m, 1H),4.46 (m, 1H), 5.84 (d, J=6.00 Hz, 1H), 6.15 (m, 1H), 7.71 (d, J=6.00 Hz,1H);

MS (ESI, Pos. 20 V): 443 (M+H)⁺, 359;

TLC: Rf 0.51 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0068(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopentylacetyl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.05 (m, 3H), 1.28 (m, 3H), 1.47 (m, 8H), 1.71 (m,11H), 1.95 (m, 1H), 2.08 (m, 1H), 2.19 (m, 1H), 2.28 (m, 2H), 2.41 (m,1H), 2.68 (m, 1H), 2.96 (m, 2H), 3.51 (m, 4H), 3.73 (m, 1H), 3.93 (m,1H), 4.39 (m, 1H), 5.84 (d, J=6.00 Hz, 1H), 6.12 (m, 1H), 7.71 (d,J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 469 (M+H)⁺, 359, 180;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0069(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-fluorobenzoyl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.36 (m, 9H), 1.67 (m, 8H), 2.01 (m, 1H), 2.24 (m, 2H),2.71 (m, 2H), 3.02 (m, 2H), 3.51 (m, 4H), 3.79 (m, 1H), 4.50 (m, 1H),5.85 (d, J=6.00 Hz, 1H), 6.22 (m, 1H), 7.22 (m, 3H), 7.47 (m, 1H), 7.71(d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 481 (M+H)⁺, 359, 241 (M+2H)²⁺, 123;

TLC: Rf 0.62 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0070N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(piperidin-1-ylcarbonyl)-1,4′-bipiperidin-3-amine

NMR (DMSO-d₆): δ 1.23 (m, 3H), 1.47 (m, 11H), 1.70 (m, 8H), 1.96 (m,1H), 2.21 (m, 1H), 2.38 (m, 2H), 2.63 (m, 3H), 2.91 (m, 1H), 3.10 (m,4H), 3.52 (m, 5H), 3.79 (m, 1H), 5.84 (d, J=6.00 Hz, 1H), 6.14 (m, 1H),7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 470 (M+H)⁺, 359, 112;

TLC: Rf 0.65 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00714-azepan-1-yl-N-(3-piperidin-1-ylcyclohexyl)pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.31 (m, 3H), 1.49 (m, 13H), 1.69 (m, 6H), 2.38 (m,5H), 3.54 (m, 4H), 4.10 (m, 1H), 5.81 (d, J=6.00 Hz, 1H), 6.07 (m, 1H),7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 358 (M+H)⁺, 179.5 (M+2H)²⁺;

TLC: Rf 0.74 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00724-azepan-1-yl-N-(1,4-trans-4-piperidin-1-ylcyclohexyl)pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.18 (m, 3H), 1.33 (m, 3H), 1.47 (m, 8H), 1.69 (m, 6H),1.94 (m, 2H), 2.20 (m, 1H), 2.42 (m, 4H), 3.57 (m, 5H), 5.81 (d, J=6.00Hz, 1H), 6.14 (m, 1H), 7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 715 (2M+H)⁺, 358 (M+H)⁺, 179.5 (M+2H)²⁺;

TLC: Rf 0.45 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00734-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanecarboxylicacid dihydrochloride

NMR (CD₃OD): δ 1.61 (m, 8H), 1.86 (m, 5H), 2.23 (m, 7H), 2.69 (m, 1H),2.84 (m, 1H), 3.05 (m, 1H), 3.51 (m, 1H), 3.72 (m, 4H), 3.96 (m, 2H),4.47 (m, 1H), 6.43 (d, J=7.50 Hz, 1H), 7.69 (d, J=7.50 Hz, 1H);

MS (ESI, Pos. 20 V): 402 (M+H)⁺, 304, 276, 201.5 (M+2H)²⁺;

TLC: Rf 0.64 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00741,4-trans-4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanol

NMR (DMSO-d₆): δ 1.12 (m, 5H), 1.42 (m, 5H), 1.63 (m, 8H), 1.79 (m, 2H),1.94 (m, 1H), 2.22 (m, 2H), 2.64 (m, 1H), 2.92 (m, 1H), 3.50 (m, 4H),3.77 (m, 2H), 4.44 (d, J=4.20 Hz, 1H), 5.82 (d, J=6.00 Hz, 1H) 6.10 (m,1H), 7.70 (d, J=6.00 Hz, 1H);

MS (FAB, Pos.): 374 (M+H)⁺;

TLC: Rf 0.33 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00754-azepan-1-yl-N-[(1R*,2R*)-2-piperidin-1-ylcyclohexyl]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.09 (m, 5H), 1.32 (m, 6H), 1.45 (m, 4H), 1.63 (m, 6H),1.83 (m, 1H), 2.31 (m, 5H), 3.57 (m, 5H), 5.74 (d, J=4.80 Hz, 1H), 5.84(d, J=6.00 Hz, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 358 (M+H)⁺, 179.5 (M+2H)²⁺;

TLC: Rf 0.43 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00761,4-4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanolnoncrystalline material;

NMR (DMSO-d₆): δ 1.29 (m, 7H), 1.46 (m, 4H), 1.68 (m, 9H), 1.95 (m, 1H),2.22 (m, 2H), 2.64 (m, 1H), 2.95 (m, 1H), 3.49 (m, 4H), 3.77 (m, 2H),4.22 (d, J=3.30 Hz, 1H), 5.83 (d, J=6.00 Hz, 1H), 6.13 (m, 1H) 7.70 (d,J=6.00 Hz, 1H);

MS (FAB, Pos.): 374 (M+H)⁺;

TLC: Rf 0.33 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00771-2-[(1-cyclohexylpiperidin-3-yl)amino]pyrimidin-4-ylazepan-4-ol

NMR (DMSO-d₆): δ 1.08 (m, 6H), 1.49 (m, 7H), 1.72 (m, 5H), 1.84 (m, 2H),2.01 (m, 1H), 2.24 (m, 2H), 2.63 (m, 1H), 2.98 (m, 1H), 3.48 (m, 4H),3.64 (m, 1H), 3.79 (m, 1H), 4.49 (d, J=3.80 Hz, 1H), 5.82 (d, J=6.00 Hz,1H), 6.10 (m, 1H), 7.71 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 374 (M+H)⁺, 292, 187.5 (M+2H)²⁺;

TLC: Rf 0.46 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0078(4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)(cyclohexyl)methanone

NMR (CDCl₃): δ 1.27 (m, 4H), 1.53 (m, 10H), 1.74 (m, 11H), 1.92 (m, 4H),2.04 (m, 1H), 2.26 (m, 2H), 2.46 (m, 4H), 2.91 (m, 1H), 3.55 (m, 4H),3.98 (m, 1H), 5.05 (m, 1H), 5.75 (m, 1H), 7.78 (m, 1H);

MS (ESI, Pos. 20 V): 468 (M+H)⁺, 276, 234.5 (M+2H)²⁺, 193;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0079N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-cyclohexyl-N²-ethylethane-1,2-diamine

NMR (DMSO-d₆): δ 0.95 (t, J=7.00 Hz, 3H), 1.16 (m, 5H), 1.41 (m, 4H),1.54 (m, 1H), 1.74 (m, 8H), 2.37 (m, 5H), 3.17 (m, 2H), 3.62 (m, 4H),5.81 (d, J=6.00 Hz, 1H), 6.17 (m, 1H), 7.69 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 346 (M+H)⁺, 264, 173.5 (M+2H)²⁺;

TLC: Rf 0.44 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0080N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-cyclohexylethane-1,2-diamine

NMR (DMSO-d₆): δ 0.92 (m, 2H), 1.19 (m, 3H), 1.45 (m, 5H), 1.63 (m, 6H),1.79 (m, 2H), 2.27 (m, 1H), 2.65 (t, J=6.50 Hz, 2H), 3.20 (m, 2H), 3.62(m, 4H), 5.83 (d, J=6.00 Hz, 1H), 6.25 (m, 1H), 7.70 (d, J=6.00 Hz, 1H);

MS (FAB, Pos.): 318 (M+H)⁺, 219, 206, 193;

TLC: Rf 0.49 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0081N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-cyclohexyl-N²-methylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.14 (m, 5H), 1.44 (m, 4H), 1.54 (m, 1H), 1.71 (m, 8H),2.19 (s, 3H), 2.30 (m, 2H), 2.42 (m, 1H), 3.18 (m, 2H), 3.62 (m, 4H),5.82 (d, J=6.00 Hz, 1H), 6.11 (m, 1H), 7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 332 (M+H)⁺, 250;

TLC: Rf 0.42 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0082N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-methyl-N²-tetrahydro-2H-pyran-4-ylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.38 (dd, J=12.40, 4.50 Hz, 1H), 1.45 (m, 5H), 1.65 (m,6H), 2.20 (s, 3H), 2.42 (m, 1H), 2.53 (m, 2H), 3.23 (m, 4H), 3.55 (m,4H), 3.85 (dd, J=11.10, 4.10 Hz, 2H), 5.83 (d, J=6.00 Hz, 1H), 6.15 (m,1H), 7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 334 (M+H)⁺, 276, 250;

TLC: Rf 0.52 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0083(1R*,2S*)-N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-cyclohexylcyclohexane-1,2-diamine

NMR (DMSO-d₆): δ 0.83 (m, 1H), 1.09 (m, 4H), 1.25 (m, 3H), 1.44 (m, 8H),1.70 (m, 10H), 2.34 (m, 1H), 2.87 (m, 1H), 3.55 (m, 4H), 3.83 (m, 1H),5.78 (m, 1H), 5.83 (d, J=6.00 Hz, 1H), 7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 290, 186.5 (M+2H)²⁺;

TLC: Rf 0.54 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0084(1R*,2R*)-N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-cyclohexylcyclohexane-1,2-diamine

NMR (DMSO-d₆): δ 0.99 (m, 8H), 1.42 (m, 6H), 1.64 (m, 10H), 1.86 (m,2H), 2.41 (m, 3H), 3.49 (m, 4H), 5.82 (d, J=6.00 Hz, 1H), 6.10 (m, 1H),7.70 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 290, 186.5 (M+2H)²⁺;

TLC: Rf 0.54 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-00853-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylacetic aciddihydrochloride

NMR (CD₃OD): δ 1.61 (m, 4H), 1.86 (m, 5H), 2.14 (m, 3H), 2.24 (m, 2H),2.49 (m, 2H), 2.92 (m, 1H), 3.06 (m, 1H), 3.23 (m, 1H), 3.65 (m, 5H),3.81 (m, 3H), 4.00 (m, 1H), 4.09 (m, 1H), 4.14 (s, 2H), 4.59 (m, 1H),6.43 (d, J=7.70 Hz, 1H), 7.69 (d, J=7.70 Hz, 1H);

MS (ESI, Pos. 20 V): 833 (2M+H)⁺, 417 (M+H)⁺, 276, 209 (M+2H)²⁺;

TLC: Rf 0.22 (CHCl₃:MeOH:NH₄OH=20:5:1).

Example 11-00863-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylpropionicacid dihydrochloride

NMR (CD₃OD): δ 1.61 (m, 4H), 1.83 (m, 5H), 2.12 (m, 3H), 2.24 (m, 2H),2.49 (m, 2H), 2.88 (t, J=6.80 Hz, 2H), 3.17 (m, 2H), 3.44 (t, J=6.80 Hz,2H), 3.69 (m, 8H), 3.98 (m, 2H), 4.07 (m, 1H), 4.56 (m, 1H), 6.43 (d,J=7.50 Hz, 1H), 7.69 (d, J=7.50 Hz, 1H);

MS (ESI, Pos. 20 V): 431 (M+H)⁺, 304, 276, 216 (M+2H)²⁺, 156;

TLC: Rf 0.22 (CHCl₃:MeOH:NH₄OH=20:5:1).

Example 11-00874-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylbutyricacid dihydrochloride

NMR (CD₃OD): δ 1.62 (m, 4H), 1.86 (m, 5H), 2.14 (m, 5H), 2.48 (m, 4H),2.90 (m, 1H), 3.12 (m, 4H), 3.72 (m, 9H), 3.99 (m, 2H), 4.07 (m, 1H),4.56 (m, 1H), 6.43 (d, J=8.10 Hz, 1H), 7.69 (d, J=8.10 Hz, 1H);

MS (ESI, Pos. 20 V): 445 (M+H)⁺, 276, 223 (M+2H)²⁺, 170;

TLC: Rf 0.22 (CHCl₃:MeOH:NH₄OH=20:5:1).

Example 11-0088 methyl(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)acetate

NMR (CDCl₃): δ 1.01 (m, 1H), 1.28 (m, 1H), 1.54 (m, 9H), 1.74 (m, 8H),1.92 (m, 2H), 2.10 (m, 1H), 2.24 (m, 3H), 2.49 (m, 2H), 2.90 (m, 1H),3.57 (m, 4H), 3.66 (s, 3H), 3.99 (m, 1H), 5.15 (m, 1H), 5.76 (m, 1H),7.79 (m, 1H);

MS (ESI, Pos. 20 V): 430 (M+H)⁺, 276, 215.5 (M+2H)²⁺, 123;

TLC: Rf 0.48 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0089 methyl3-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)propanoate

NMR (CDCl₃): δ 0.93 (m, 1H), 1.24 (m, 1H), 1.54 (m, 11H), 1.74 (m, 8H),2.00 (m, 2H), 2.28 (m, 4H), 2.48 (m, 2H), 2.91 (m, 1H), 3.58 (m, 4H),3.67 (s, 3H), 3.99 (m, 1H), 5.12 (m, 1H), 5.76 (m, 1H), 7.79 (m, 1H);

MS (ESI, Pos. 20 V): 444 (M+H)⁺, 276, 222.5 (M+2H)²⁺, 137;

TLC: Rf 0.48 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0090(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)aceticacid hydrochloride

NMR (CD₃OD): δ 1.18 (m, 1H), 1.61 (m, 4H), 1.85 (m, 6H), 1.97 (m, 2H),2.17 (m, 6H), 2.42 (m, 2H), 2.86 (m, 1H), 3.04 (m, 1H), 3.24 (m, 1H),3.53 (m, 1H), 3.70 (m, 3H), 3.83 (m, 1H), 3.92 (m, 1H), 4.05 (m, 1H),4.52 (m, 1H), 5.00 (d, J=4.80 Hz, 1H), 6.43 (d, J=7.70 Hz, 1H), 7.70 (d,J=7.70 Hz, 1H);

MS (ESI, Pos. 20 V): 416 (M+H)⁺, 276, 208.5 (M+2H)²⁺, 123;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=20:5:1).

Example 11-00913-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)propionic acid hydrochloride

NMR (CD₃OD): δ 1.10 (m, 1H), 1.62 (m, 4H), 1.86 (m, 10H), 2.23 (m, 6H),2.49 (t, J=8.20 Hz, 2H), 2.85 (m, 1H), 3.04 (m, 1H), 3.24 (m, 1H), 3.56(m, 1H), 3.72 (m, 2H), 3.84 (m, 2H), 3.97 (m, 3H), 4.48 (m, 1H), 6.43(d, J=7.70 Hz, 1H), 7.69 (d, J=7.70 Hz, 1H);

MS (ESI, Pos. 20 V): 430 (M+H)⁺, 276, 215.5 (M+2H)²⁺, 138;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=20:5:1).

Example 11-00923-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N,N-dimethyl-1,4′-bipiperidine-1′-sulfonamide

NMR (CDCl₃): δ 1.55 (m, 8H), 1.75 (m, 8H), 2.27 (m, 1H), 2.38 (m, 1H),2.47 (m, 1H), 2.57 (m, 1H), 2.79 (m, 2H), 2.80 (s, 6H), 2.93 (m, 1H),3.59 (m, 4H), 3.73 (m, 2H), 4.00 (m, 1H), 5.38 (m, 1H), 5.78 (d, J=6.20Hz, 1H), 7.77 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 931 (2M+H)⁺, 466 (M+H)⁺, 276, 211;

TLC: Rf 0.35 (CHCl₃:MeOH=10:1).

Example 11-00934-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-(cyclohexylmethyl)oxime

NMR (CDCl₃): δ 0.95 (m, 2H), 1.23 (m, 3H), 1.54 (m, 8H), 1.72 (m, 12H),1.92 (m, 2H), 2.08 (m, 1H), 2.28 (m, 1H), 2.49 (m, 4H), 2.92 (m, 1H),3.21 (m, 1H), 3.56 (m, 5H), 3.80 (d, J=6.40 Hz, 2H), 4.00 (m, 1H), 5.08(m, 1H), 5.76 (d, J=6.00 Hz, 1H), 7.79 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 966 (2M+H)⁺, 483 (M+H)⁺, 242 (M+2H)²⁺;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00944-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-cycloheptyloxime

NMR (CDCl₃): δ 1.54 (m, 18H), 1.75 (m, 5H), 1.85 (m, 2H), 1.94 (m, 3H),2.07 (m, 1H), 2.28 (m, 1H), 2.50 (m, 4H), 2.92 (m, 1H), 3.22 (m, 1H),3.56 (m, 4H), 3.74 (m, 1H), 3.99 (m, 1H), 4.16 (m, 1H), 5.08 (m, 1H),5.76 (d, J=6.00 Hz, 1H), 7.79 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 966 (2M+H)⁺, 483 (M+H)⁺, 276, 194;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00954-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-cyclohexyloxime

NMR (CDCl₃): δ 1.33 (m, 5H), 1.54 (m, 8H), 1.74 (m, 8H), 1.82 (m, 2H),1.90 (m, 3H), 2.08 (m, 1H), 2.28 (m, 1H), 2.49 (m, 4H), 2.93 (m, 1H),3.25 (m, 1H), 3.56 (m, 5H), 3.98 (m, 2H), 5.07 (m, 1H), 5.76 (d, J=6.00Hz, 1H), 7.79 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 469 (M+H)⁺, 276, 194;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-00964-azepan-1-yl-N-[1,4-trans-1-(4-phenoxycyclohexyl)piperidin-3-yl]pyrimidin-2-amine

NMR (CDCl₃): δ 0.85 (m, 1H), 1.42 (m, 4H), 1.54 (m, 4H), 1.75 (m, 8H),1.92 (m, 2H), 2.18 (m, 1H), 2.28 (m, 1H), 2.43 (m, 2H), 2.58 (m, 1H),2.96 (m, 1H), 3.58 (m, 4H), 4.00 (m, 1H), 4.12 (m, 1H), 5.34 (m, 1H),5.78 (d, J=6.00 Hz, 1H), 6.88 (d, J=7.50 Hz, 2H), 6.92 (t, J=7.50 Hz,1H), 7.26 (t, J=7.50 Hz, 2H), 7.77 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 899 (2M+H)⁺, 450 (M+H)⁺, 276;

TLC: Rf 0.23 (CHCl₃:MeOH=10:1).

Example 11-0097 benzyl4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexylcarbamate

NMR (CDCl₃): δ 1.12 (m, 1H), 1.53 (m, 10H), 1.74 (m, 8H), 2.05 (m, 1H),2.24 (m, 2H), 2.47 (m, 2H), 2.88 (m, 1H), 3.56 (m, 4H), 3.78 (m, 1H),3.99 (m, 1H), 4.98 (m, 1H), 5.09 (s, 2H), 5.37 (m, 1H), 5.76 (d, J=6.20Hz, 1H), 7.36 (m, 5H), 7.76 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 507 (M+H)⁺, 415, 373, 276;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0098 benzyl(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)methylcarbamate

NMR (CDCl₃): δ 0.96 (m, 1H), 1.53 (m, 11H), 1.74 (m, 8H), 2.09 (m, 1H),2.26 (m, 2H), 2.46 (m, 2H), 2.84 (m, 1H), 3.09 (m, 2H), 3.56 (m, 4H),3.99 (m, 1H), 4.81 (m, 1H), 5.10 (s, 2H), 5.21 (m, 1H), 5.76 (d, J=6.20Hz, 1H), 7.35 (m, 5H), 7.78 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 521 (M+H)⁺, 431, 387, 276;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0099N-(4-azepan-1-ylpyrimidin-2-yl)-1-methylpiperidine-3-carboxamide

NMR (DMSO-d₆): δ 1.41 (m, 6H), 1.68 (m, 6H), 1.87 (m, 1H), 2.00 (m, 1H),2.14 (s, 3H), 2.61 (m, 1H), 2.74 (m, 1H), 2.97 (m, 1H), 3.48 (m, 2H),3.70 (m, 2H), 6.31 (d, J=6.2 Hz, 1H) 7.96 (d, J=6.2 Hz, 1H), 9.90 (s,1H);

MS (FAB, Pos.): 318 (M+H)⁺;

TLC: Rf 0.52 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0100N-[1-(4-aminocyclohexyl)piperidin-3-yl]-4-azepan-1-ylpyrimidin-2-amine

NMR (CDCl₃): δ 1.22 (m, 1H), 1.55 (m, 7H), 1.76 (m, 12H), 2.25 (m, 1H),2.44 (m, 1H), 2.59 (m, 1H), 2.75 (m, 0.5H), 2.96 (m, 0.5H), 3.14 (m,2H), 3.57 (m, 4H), 4.02 (m, 1H), 5.30 (m, 0.5H), 5.79 (m, 1.5H), 7.75(m, 1H);

MS (ESI, Pos. 20 V): 373 (M+H)⁺, 178;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:20:2).

Example 11-0101N-1-[4-(aminomethyl)cyclohexyl]piperidin-3-yl-4-azepan-1-ylpyrimidin-2-amine

NMR (CDCl₃): δ 0.93 (m, 1H), 1.24 (m, 2H), 1.54 (m, 8H), 1.65 (m, 3H),1.75 (m, 5H), 1.86 (m, 2H), 2.26 (m, 2H), 2.50 (m, 2H), 2.63 (m, 2H),2.85 (m, 0.5H), 2.97 (m, 0.5H), 3.57 (m, 4H), 4.00 (m, 1H), 5.18 (m,1H), 5.76 (d, J=6.20 Hz, 1H), 7.79 (m, 1H);

MS (ESI, Pos. 20 V): 387 (M+H)⁺, 276, 194 (M+2H)²⁺, 185;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:20:2).

Example 11-01024-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-yl-1-methylcyclohexanol

NMR (CDCl₃): δ 1.22 (m, 3H), 1.42 (m, 3H), 1.54 (m, 5H), 1.64 (m, 4H),1.75 (m, 8H), 2.28 (m, 2H), 2.47 (m, 1H), 2.57 (m, 1H), 2.95 (m, 1H),3.58 (m, 4H), 3.77 (m, 1H), 4.00 (m, 1H), 5.16 (m, 1H), 5.76 (m, 1H),7.79 (m, 1H);

MS (ESI, Pos. 20 V): 388 (M+H)⁺, 304, 276, 193;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0103N-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)methanesulfonamide

NMR (CDCl₃): δ 1.30 (m, 2H), 1.54 (m, 5H), 1.61 (m, 3H), 1.74 (m, 6H),1.85 (m, 2H), 2.11 (m, 1H), 2.25 (m, 1H), 2.42 (m, 2H), 2.52 (m, 2H),2.76 (m, 1H), 2.89 (m, 0.5H), 2.97 (s, 3H), 3.21 (m, 0.5H), 3.57 (m,4H), 4.02 (m, 1H), 4.60 (m, 0.5H), 4.93 (m, 0.5H), 5.20 (m, 1H), 5.76(m, 1H), 7.78 (m, 1H);

MS (ESI, Pos. 20 V): 451 (M+H)⁺, 356, 276, 226 (M+2H)²⁺, 178;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0104N-[(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)methyl]methanesulfonamide

NMR (CDCl₃): δ 0.98 (m, 1H), 1.26 (m, 1H), 1.54 (m, 10H), 1.74 (m, 8H),1.87 (m, 1H), 2.03 (m, 1H), 2.36 (m, 3H), 2.56 (m, 0.5H), 2.75 (m,0.5H), 2.95 (m, 4H), 3.08 (m, 1 H) 3.56 (m, 4H), 4.02 (m, 1H), 4.43 (m,0.5H), 4.69 (m, 0.5H), 5.21 (m, 1H), 5.76 (d, J=6.00 Hz, 1H), 7.78 (d,J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 465 (M+H)⁺, 276, 233 (M+2H)²⁺, 138;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0105N-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)cyclohexanecarboxamide

NMR (CDCl₃): δ 1.11 (m, 1H), 1.25 (m, 2H), 1.54 (m, 10H), 1.75 (m, 15H),2.04 (m, 2H), 2.23 (m, 1H), 2.41 (m, 3H), 2.87 (m, 1H), 3.56 (m, 5H),4.00 (m, 2H), 5.13 (m, 1.5H), 5.61 (m, 0.5H), 5.77 (m, 1H), 7.79 (d,J=6.20 Hz, 1H);

MS (FAB, Pos., matrix=Glycerin+m-NBA): 483 (M+H)⁺, 193;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:10:1).

Example 11-0106N-[(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)methyl]cyclohexanecarboxamide

NMR (CDCl₃): δ 0.97 (m, 1H), 1.25 (m, 4H), 1.54 (m, 11H), 1.75 (m, 15H),2.06 (m, 1H), 2.29 (m, 2H), 2.47 (m, 2H), 2.89 (m, 1H), 3.08 (m, 1H),3.21 (m, 1H), 3.57 (m, 4H), 4.02 (m, 1H), 5.46 (m, 1H), 5.63 (m, 1H),5.78 (m, 1H), 7.76 (m, 1H);

MS (FAB, Pos., matrix=Glycerin+m-NBA): 497 (M+H)⁺, 193;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0107N-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)acetamide

NMR (CDCl₃): δ 1.13 (m, 1H), 1.55 (m, 11H), 1.74 (m, 8H), 1.96 (m, 3H),2.33 (m, 3.5H), 2.55 (m, 0.5H), 2.72 (m, 0.5H), 2.92 (m, 0.5H), 3.58 (m,4H), 4.01 (m, 2H), 5.15 (m, 0.5H), 5.32 (m, 1H), 5.76 (m, 1H), 5.94 (m,0.5H), 7.78 (m, 1H);

MS (ESI, Pos. 20 V): 415 (M+H)⁺, 276, 208 (M+2H)²⁺, 140;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0108N-[(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)methyl]acetamide

NMR (CDCl₃): δ 0.97 (m, 1H), 1.25 (m, 1H), 1.54 (m, 9H), 1.74 (m, 6H),1.86 (m, 4H), 1.99 (m, 3H), 2.24 (m, 1H), 2.43 (m, 3H), 2.74 (m, 0.5H),2.94 (m, 0.5H), 3.17 (m, 2H), 3.56 (m, 4H), 4.02 (m, 1H), 5.20 (m, 1H),5.49 (m, 0.5H), 5.76 (m, 1H), 5.81 (m, 0.5H), 7.78 (m, 1H);

MS (ESI, Pos. 20 V): 429 (M+H)⁺, 276, 215 (M+2H)²⁺, 154;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0109N-(4-azepan-1-ylpyrimidin-2-yl)-1-methylpiperidine-2-carboxamide

NMR (CDCl₃): δ 1.68 (m, 12H), 2.08 (m, 3H), 2.29 (s, 3H), 2.64 (m, 1H),2.97 (m, 1H), 3.63 (m, 4H), 6.14 (d, J=6.2 Hz, 1H), 8.09 (d, J=6.2 Hz,1H), 8.84 (s, 1H);

MS (FAB, Pos.): 318 (M+H)⁺;

TLC: Rf 0.50 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0110N′-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)-N,N-dimethylsulfamide

NMR (CDCl₃): δ 1.26 (m, 2H), 1.57 (m, 8H), 1.75 (m, 8H), 2.07 (m, 2H),2.29 (m, 2H), 2.47 (m, 2H), 2.79 (m, 6H), 2.97 (m, 1H), 3.54 (m, 4.5H),4.01 (m, 1.5H), 4.47 (m, 1H), 5.18 (m, 1H), 5.76 (m, 1H), 7.78 (m, 1H);

MS (FAB, pos. matrix=Glycerin+m-NBA): 480 (M+H)⁺, 371, 287, 243, 217,193, 122;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0111N′-[(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)methyl]-N,N-dimethylsulfamide

NMR (CDCl₃): δ 0.97 (m, 1H), 1.26 (m, 1H), 1.54 (m, 10H), 1.74 (m, 4H),1.87 (m, 3H), 2.26 (m, 2H), 2.45 (m, 2H), 2.57 (m, 1H), 2.81 (m, 6H),2.88 (m, 1H), 3.00 (m, 1H), 3.57 (m, 5H), 4.01 (m, 1.5H), 4.13 (m,0.5H), 4.31 (m, 0.5H), 4.81 (m, 0.5H), 5.16 (m, 1H), 5.76 (d, J=6.20 Hz,1H), 7.78 (d, J=6.20 Hz, 1H);

MS (FAB, Pos., matrix=Glycerin+m-NBA): 494 (M+H)⁺, 301, 257, 217, 193,122;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0112N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cycloheptylcarbonyl)-1,4′-bipiperidin-3-amine

NMR (CDCl₃): δ 1.55 (m, 13H), 1.75 (m, 15H), 2.26 (m, 1H), 2.53 (m, 5H),2.97 (m, 2H), 3.56 (m, 4H), 3.95 (m, 2H), 4.65 (m, 1H), 5.08 (m, 1H),5.77 (d, J=6.20 Hz, 1H), 7.79 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 483 (M+H)⁺, 359;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0113N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(tetrahydro-2H-pyran-4-ylcarbonyl)-1,4′-bipiperidin-3-amine

NMR (CDCl₃): δ 1.55 (m, 9H), 1.74 (m, 6H), 1.84 (m, 5H), 2.27 (m, 1H),2.52 (m, 4H), 2.73 (m, 1H), 2.96 (m, 2H), 3.44 (m, 2H), 3.57 (m, 4H),3.99 (m, 4H), 4.65 (m, 1H), 5.18 (m, 1H), 5.77 (d, J=6.20 Hz, 1H), 7.78(d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 471 (M+H)⁺, 359, 304;

TLC: Rf 0.33 (AcOEt:MeOH:TEA=20:2:1).

Example 11-01144-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-yl-1-phenylcyclohexanol

NMR (CDCl₃): δ 1.54 (m, 7H), 1.80 (m, 13H), 2.43 (m, 4H), 2.64 (m, 1H),3.03 (m, 1H), 3.55 (m, 4H), 4.01 (m, 1H), 5.13 (m, 1H), 5.75 (m, 1H),7.24 (m, 1H), 7.34 (m, 2H), 7.51 (m, 2H), 7.77 (m, 1H);

MS (FAB, pos. matrix=Glycerin+m-NBA): 450 (M+H)⁺;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0115N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-methylethane-1,2-diamine

NMR (CDCl₃): δ 1.54 (m, 4H), 1.74 (m, 4H), 2.71 (s, 3H), 3.24 (t, J=5.20Hz, 2H), 3.43 (m, 3H), 3.77 (m, 4H), 5.81 (d, J=6.60 Hz, 1H), 7.54 (m,1H), 7.65 (d, J=6.60 Hz, 1H);

MS (ESI, Pos. 20 V): 250 (M+H)⁺, 125;

TLC: Rf 0.33 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-01164-azepan-1-yl-N-[(3S)-1-(1,4-dioxaspiro[4.5]dec-8-yl)piperidin-3-yl]pyrimidin-2-amine

NMR (CDCl₃): δ 1.53 (m, 8H), 1.72 (m, 12H), 2.30 (m, 2H), 2.55 (m, 2H),2.95 (m, 1H), 3.58 (m, 4H), 3.92 (s, 4H), 4.02 (m, 1H), 5.09 (m, 1H),5.76 (d, J=6.00 Hz, 1H), 7.79 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 416 (M+H)⁺, 276, 208.5 (M+2H)²⁺;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0117N-(1-benzylpiperidin-3-yl)-4-(1,4-oxazepan-4-yl)pyrimidin-2-amine

NMR (CDCl₃): δ 1.55 (m, 1H), 1.71 (m, 3H), 1.95 (m, 2H), 2.29 (m, 1H),2.39 (m, 2H), 2.72 (m, 1H), 3.46 (d, J=13.00 Hz, 1H), 3.52 (d, J=13.00Hz, 1H), 3.68 (m, 4H), 3.74 (m, 4H), 4.02 (m, 1H), 5.15 (m, 1H), 5.77(d, J=6.00 Hz, 1H), 7.28 (m, 5H), 7.83 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 368 (M+H)⁺, 278;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0118 4-(1,4-oxazepan-4-yl)-N-piperidin-3-ylpyrimidin-2-amine

NMR (CDCl₃): δ 1.50 (m, 1H), 1.71 (m, 1H), 1.86 (m, 2H), 1.96 (m, 2H),2.53 (m, 1H), 2.66 (m, 1H), 2.86 (m, 1H), 3.21 (m, 1H), 3.69 (m, 4H),3.76 (m, 4H), 3.85 (m, 1H), 4.93 (m, 1H), 5.78 (d, J=6.00 Hz, 1H), 7.82(d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 278 (M+H)⁺, 139.5 (M+2H)²⁺;

TLC: Rf 0.44 (CHCl₃:MeOH:NH₄OH=80:20:4).

Example 11-0119 ethyl4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanecarboxylate

NMR (CDCl₃): δ 1.24 (m, 3H), 1.52 (m, 11H), 1.72 (m, 7H), 1.89 (m, 1H),2.03 (m, 2H), 2.21 (m, 2H), 2.40 (m, 1H), 2.51 (m, 1H), 2.91 (m, 1H),3.55 (m, 4H), 3.97 (m, 1H), 4.11 (m, 2H), 5.17 (m, 1H), 5.74 (m, 1H),7.76 (d, J=6.20 Hz, 1H);

MS (ESI, Pos. 20 V): 430 (M+H)⁺, 276, 215.5 (M+2H)²⁺;

TLC: Rf 0.52 (AcOEt:MeOH:TEA=20:2:1).

Example 11-01204-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-yl-N-methoxy-N-methylcyclohexanecarboxamide

NMR (CDCl₃): δ 1.51 (m, 9H), 1.71 (m, 6H), 1.90 (m, 4H), 2.24 (m, 1H),2.37 (m, 2H), 2.54 (m, 2H), 2.79 (m, 1H), 2.91 (m, 1H), 3.13 (m, 3H),3.56 (m, 4H), 3.65 (m, 3H), 3.98 (m, 1H), 5.10 (m, 1H), 5.73 (m, 1H),7.75 (m, 1H);

MS (ESI, Pos. 20 V): 445 (M+H)⁺, 384, 276, 223 (M+2H)²⁺, 170;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 11-01214-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanecarboaldehyde

NMR (CDCl₃): δ 1.29 (m, 4H), 1.54 (m, 6H), 1.74 (m, 6H), 2.01 (m, 4H),2.28 (m, 3H), 2.53 (m, 2H), 2.95 (m, 1H), 3.56 (m, 4H), 3.98 (m, 1H),5.16 (m, 1H), 5.76 (d, J=6.00 Hz, 1H), 7.78 (d, J=6.00 Hz, 1H), 9.61 (s,1H);

MS (ESI, Pos. 20 V): 386 (M+H)⁺, 276, 193.5 (M+2H)²⁺;

TLC: Rf 0.48 (AcOEt:MeOH:TEA=20:2:1).

Example 11-0122(4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexyl)(cyclohexyl)methanol

NMR (CDCl₃): δ 1.23 (m, 6H), 1.54 (m, 12H), 1.75 (m, 12H), 2.04 (m, 2H),2.25 (m, 2H), 2.40 (m, 2H), 2.56 (m, 2H), 2.97 (m, 1H), 3.55 (m, 4H),4.02 (m, 1H), 5.39 (m, 1H), 5.76 (d, J=6.20 Hz, 1H), 7.77 (m, 1H);

MS (ESI, Pos. 20 V): 470 (M+H)⁺, 276, 235.5 (M+2H)²⁺;

TLC: Rf 0.48 (AcOEt:MeOH:TEA=20:2:1).

Example 11-01234-azepan-1-yl-N-(1-benzylpyrrolidin-3-yl)pyrimidin-2-amine

NMR (DMSO-d₆, 363.1K): δ 1.48 (m, 4H), 1.68 (m, 6H), 2.13 (m, 1H), 2.38(dd, J=9.3, 5.2 Hz, 1H), 2.58 (m, 1H), 2.84 (dd, J=9.3, 6.9 Hz, 1H),3.53 (t, J=6.00 Hz, 4H), 3.59 (s, 2H), 4.27 (m, 1H), 5.83 (d, J=6.04 Hz,1H), 5.94 (m, 1H), 7.24 (m, 5H). 7.71 (d, J=6.04 Hz, 1H);

MS (ESI, Pos. 20 V): 352 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.00;

TLC: Rf 0.16 (CH₃C1: MeOH:NH₄OH=80:10:1).

Example 11-0124 1-[2-(4-phenylpiperazin-1-yl)pyrimidin-4-yl]azepane

NMR (DMSO-d₆, 363.1K): δ 1.52 (m, 4H), 1.72 (m, 4H), 3.20 (t, J=5.10 Hz,4H), 3.60 (t, J=6.00 Hz, 4H), 3.83 (t, J=5.10 Hz, 4H), 5.93 (d, J=6.04Hz, 1H), 6.79 (t, J=7.3 Hz, 1H), 6.97 (d, J=7.7 Hz, 2H), 7.23 (m, 2H),7.86 (d, J=6.04 Hz, 1H);

MS (ESI, Pos. 20 V): 338 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.40;

TLC: Rf 0.18 (Hexane:AcOEt=3:1).

Example 11-0125 1-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]azepane

NMR (DMSO-d₆, 363.1K): δ 1.49 (m, 4H), 1.71 (m, 4H), 2.20 (s, 3H), 2.32(t, J=5.10 Hz, 4H), 3.56 (t, J=6.00 Hz, 4H), 3.65 (t, J=5.10 Hz, 4H),5.88 (d, J=6.0 Hz, 1H), 7.80 (d, J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 276 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.76;

TLC: Rf 0.18 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0126 1-[2-(4-benzylpiperazin-1-yl)pyrimidin-4-yl]azepane

NMR (DMSO-d₆, 363.1K): δ 1.48 (m, 4H), 1.68 (m, 4H), 2.40 (t, J=5.10 Hz,4H), 3.50 (s, 2H), 3.54 (t, J=5.70 Hz, 4H), 3.65 (t, J=5.10 Hz, 4H),5.87 (d, J=6.0 Hz, 1H), 7.26 (m, 5H), 7.79 (d, J=6.0 Hz, 1H);

MS (ESI, Pos. 20 V): 352 (M+H)⁺; HPLC condition: A; HPLC retention time(min): 2.96;

TLC: Rf 0.41 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-01273-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylacetic acid Example11-01284-azepan-1-yl-N-[1-(cyclopropylmethyl)pyrrolidin-3-yl]pyrimidin-2-amineExample 11-01294-azepan-1-yl-N-1-[3-(methylsulfanyl)propyl]pyrrolidin-3-ylpyrimidin-2-amineExample 11-01304-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylbutyric acidExample 11-01314-azepan-1-yl-N-[1-(2,6-dimethylhept-5-enyl)pyrrolidin-3-yl]pyrimidin-2-amineExample 11-01324-azepan-1-yl-N-[1-(quinolin-2-ylmethyl)pyrrolidin-3-yl]pyrimidin-2-amineExample 11-01332-(acetylamino)-1-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-yl-1,2-dideoxy-D-galactitolExample 11-01344-azepan-1-yl-N-(1-neopentylpyrrolidin-3-yl)pyrimidin-2-amine Example11-01354-azepan-1-yl-N-1-[(2E)-3-(2-furyl)prop-2-enyl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 368 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.97.

Example 11-01364-azepan-1-yl-N-1-[4-(octyloxy)benzyl]pyrrolidin-3-ylpyrimidin-2-amineExample 11-01374-azepan-1-yl-N-(1-isobutylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 318 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 4.15.

Example 11-01384-azepan-1-yl-N-(1-propylpyrrolidin-3-yl)pyrimidin-2-amine Example11-01394-azepan-1-yl-N-1-[(2E)-dec-2-enyl]pyrrolidin-3-ylpyrimidin-2-amineExample 11-01404-azepan-1-yl-N-1-[2-(benzyloxy)ethyl]pyrrolidin-3-ylpyrimidin-2-amineExample 11-01414-4-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylbutyric acidExample 11-01422-(acetylamino)-1-4-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-yl-1,2-dideoxy-D-galactitolExample 11-01434-azepan-1-yl-N-(1-benzylpiperidin-4-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 731 (2M+H)⁺, 366 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 4.11.

Example 11-01444-azepan-1-yl-N-1-[(2E)-3-(2-furyl)prop-2-enyl]piperidin-4-ylpyrimidin-2-amineExample 11-01454-azepan-1-yl-N-[1-(2-ethylhexyl)piperidin-4-yl]pyrimidin-2-amineExample 11-01462-4-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylethanol Example11-01474-azepan-1-yl-N-1-[(2E)-dec-2-enyl]piperidin-4-ylpyrimidin-2-amineExample 11-01484-azepan-1-yl-N-[1-(4-[(2E)-4-methylpent-2-enyl]cyclohex-3-en-1-ylmethyl)piperidin-4-yl]pyrimidin-2-amineExample 11-01495-methyl-3-phenyl-N-2-[(4-pyrrolidin-1-ylpyrimidin-2-yl)amino]ethylisoxazole-4-carboxamide

MS (ESI, Pos.20V): 785 (2M+H)⁺, 393 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0150N-2-[(4-piperidin-1-ylpyrimidin-2-yl)amino]ethylbenzamide

MS (ESI, Pos.20V): 326 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-01515-methyl-3-phenyl-N-2-[(4-piperidin-1-ylpyrimidin-2-yl)amino]ethylisoxazole-4-carboxamide

MS (ESI, Pos.20V): 813 (2M+H)⁺, 407 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0152N-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethyl-2,2-diphenylacetamide

MS (ESI, Pos.20V): 859 (2M+H)⁺, 430 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.49.

Example 11-0153N-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethyl-5-methyl-3-phenylisoxazole-4-carboxamide

MS (ESI, Pos.20V): 841 (2M+H)⁺, 421 (M+H);

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-0154 N-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethylacrylamide

MS (ESI, Pos.20V): 290 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0155N-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethylcyclohexanecarboxamide

MS (ESI, Pos.20V): 346 (M+H)⁺, 267;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0156N-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethyl-3-cyclopentylpropanamide

MS (ESI, Pos.20V): 719 (2M+H)⁺, 360 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-0157N-(2-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]aminoethyl)-2,2-diphenylacetamide

MS (ESI, Pos.20V): 927 (2M+H)⁺, 464 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.56.

Example 11-0158N-(2-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]aminoethyl)-5-methyl-3-phenylisoxazole-4-carboxamide

MS (ESI, Pos.20V): 455 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-0159N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-methyl-N²-(quinolin-2-ylmethyl)ethane-1,2-diamineExample 11-0160 butylN-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethyl-N-methylglycinate Example11-0161N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²-[(2E)-3,7-dimethyloct-2,6-dienyl]-N²-methylethane-1,2-diamineExample 11-0162 butyl(2-[(4-azepan-1-ylpyrimidin-2-yl)amino]methylpyrrolidin-1-yl)acetateExample 11-0163 ethylN-2-[(4-azepan-1-ylpyrimidin-2-yl)amino]ethyl-N-methylglycinate Example11-0164 ethyl(2-[(4-azepan-1-ylpyrimidin-2-yl)amino]methylpyrrolidin-1-yl)acetateExample 11-0165 N-(4-pyrrolidin-1-ylpyrimidin-2-yl)ethane-1,2-diamine

MS (ESI, Pos.20V): 208 (M+H);

HPLC condition: B; HPLC retention time (min): 2.86.

Example 11-0166 1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpyrrolidin-3-olExample 11-0167N-[4-(4-phenylpiperazin-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 299 (M+H);

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-0168N-[4-(4-methylpiperazin-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 237 (M+H);

HPLC condition: B; HPLC retention time (min): 2.59.

Example 11-0169 N-(4-morpholin-4-ylpyrimidin-2-yl)ethane-1,2-diamineExample 11-0170 N-(4-thiomorpholin-4-ylpyrimidin-2-yl)ethane-1,2-diamine

MS (ESI, Pos.20V): 240 (M+H);

HPLC condition: B; HPLC retention time (min): 2.89.

Example 11-01712-(1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperidin-2-yl)ethanol

MS (ESI, Pos.20V): 266 (M+H);

HPLC condition: A; HPLC retention time (min): 2.73.

Example 11-0172(1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperidin-3-yl)methanol

MS (ESI, Pos.20V): 252 (M+H);

HPLC condition: B; HPLC retention time (min): 2.74.

Example 11-0173 1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperidin-4-ol

MS (ESI, Pos.20V): 238 (M+H);

HPLC condition: B; HPLC retention time (min): 2.41.

Example 11-0174N-[4-(4-phenyl-3,6-dihydropyridin-1(2H)-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 296 (M+H);

HPLC condition: A; HPLC retention time (min): 3.08.

Example 11-01752-(1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperidin-4-yl)ethanol

MS (ESI, Pos.20V): 266 (M+H);

HPLC condition: A; HPLC retention time (min): 2.63.

Example 11-0176 1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperidin-3-ol

MS (ESI, Pos.20V): 238 (M+H);

HPLC condition: B; HPLC retention time (min): 2.57.

Example 11-0177N-[4-(3,6-dihydropyridin-1(2H)-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 220 (M+H);

HPLC condition: A; HPLC retention time (min): 2.70.

Example 11-01784-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperazine-1-carboaldehydeExample 11-01792-(4-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperazin-1-yl)ethanol Example11-0180N-[4-(3,5-dimethylpiperidin-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 250 (M+H);

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0181 N-(4-azepan-1-ylpyrimidin-2-yl)ethane-1,2-diamine

MS (ESI, Pos.20V): 236 (M+H);

HPLC condition: A; HPLC retention time (min): 2.84.

Example 11-0182N-[4-(4-methyl-1,4-diazepan-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 251 (M+H);

HPLC condition: B; HPLC retention time (min): 2.68.

Example 11-0183N-[4-(2,6-dimethylmorpholin-4-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 252 (M+H);

HPLC condition: A; HPLC retention time (min): 2.68.

Example 11-0184N-4-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]pyrimidin-2-ylethane-1,2-diamine

MS (ESI, Pos.20V): 252 (M+H);

HPLC condition: A; HPLC retention time (min): 2.71.

Example 11-0185 ethyl1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperidine-3-carboxylate

MS (ESI, Pos.20V): 294 (M+H);

HPLC condition: A; HPLC retention time (min): 2.85.

Example 11-0186 ethyl1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperidine-4-carboxylate

MS (ESI, Pos.20V): 294 (M+H);

HPLC condition: A; HPLC retention time (min): 2.85.

Example 11-0187N-[4-(4-phenylpiperidin-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 298 (M+H);

HPLC condition: A; HPLC retention time (min): 3.08.

Example 11-0188N-[4-(4-benzylpiperidin-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 312 (M+H);

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0189N-[4-(1,4′-bipiperidin-1′-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 305 (M+H);

HPLC condition: B; HPLC retention time (min): 3.14.

Example 11-0190N-4-[4-(4-methoxyphenyl)piperazin-1-yl]pyrimidin-2-ylethane-1,2-diamine

MS (ESI, Pos.20V): 329 (M+H);

HPLC condition: A; HPLC retention time (min): 2.81.

Example 11-0191N-(4-4-[4-(trifluoromethyl)phenyl]piperazin-1-ylpyrimidin-2-yl)ethane-1,2-diamine

MS (ESI, Pos.20V): 367 (M+H);

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0192N-[4-(4-cyclohexylpiperazin-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 305 (M+H);

HPLC condition: B; HPLC retention time (min): 3.29.

Example 11-0193N-[4-(4-benzylpiperazin-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 313 (M+H);

HPLC condition: B; HPLC retention time (min): 3.27.

Example 11-0194N-4-[4-(2,4-dimethylphenyl)piperazin-1-yl]pyrimidin-2-ylethane-1,2-diamine

MS (ESI, Pos.20V): 327 (M+H);

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0195N-(4-4-[(2E)-3-phenylprop-2-enyl]piperazin-1-ylpyrimidin-2-yl)ethane-1,2-diamine

MS (ESI, Pos.20V): 339 (M+H);

HPLC condition: A; HPLC retention time (min): 2.86.

Example 11-0196N-4-[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]pyrimidin-2-ylethane-1,2-diamine

MS (ESI, Pos.20V): 334 (M+H);

HPLC condition: B; HPLC retention time (min): 2.77.

Example 11-0197 ethyl4-2-[(2-aminoethyl)amino]pyrimidin-4-ylpiperazine-1-carboxylate

MS (ESI, Pos.20V): 295 (M+H);

HPLC condition: A; HPLC retention time (min): 2.78.

Example 11-0198N-(4-4-[5-(trifluoromethyl)pyridin-2-yl]-1,4-diazepan-1-ylpyrimidin-2-yl)ethane-1,2-diamine

MS (ESI, Pos.20V): 382 (M+H);

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0199N-(1-2-[(2-aminoethyl)amino]pyrimidin-4-ylpyrrolidin-3-yl)-N-methylacetamide

MS (ESI, Pos.20V): 279 (M+H);

HPLC condition: B; HPLC retention time (min): 2.57.

Example 11-0200N-[4-(2-pyridin-2-ylazepan-1-yl)pyrimidin-2-yl]ethane-1,2-diamine

MS (ESI, Pos.20V): 313 (M+H);

HPLC condition: A; HPLC retention time (min): 2.74.

Example 11-0201(3R)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-benzylazepan-3-amine

NMR (DMSO-d₆): 1.36 (m, 5H), 1.59 (m, 8H), 1.82 (m, 1H), 2.56 (m, 3H),2.80 (m, 1H), 3.48 (m, 4H), 3.63 (s, 2H), 3.95 (m, 1H), 5.80 (d, J=5.90Hz, 1H), 6.08 (m, 1H), 7.24 (m, 5H), 7.68 (d, J=5.90 Hz, 1H);

MS (ESI, Pos. 20 V): 380 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 3.03;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0202 (3R)-N-(4-azepan-1-ylpyrimidin-2-yl)azepan-3-amine

NMR (DMSO-d₆): δ 1.44 (m, 5H), 1.61 (m, 9H), 2.60 (dd, J=13.50, 7.10 Hz,1H), 2.72 (t, J=6.00 Hz, 2H), 2.89 (dd, J=13.50, 4.30 Hz, 1H), 3.56 (m,4H), 3.87 (m, 1H), 5.81 (d, J=6.00 Hz, 1H), 6.09 (m, 1H), 7.70 (d,J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 290 (M+H)⁺, 145.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.92;

TLC: Rf 0.20 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 11-0203(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-(pyridin-2-ylmethyl)azepan-3-amineExample 11-0204(3R)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-(pyridin-2-ylmethyl)azepan-3-amineExample 11-0205(3R)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2-ethylbutyl)azepan-3-amine

MS (ESI, Pos. 20 V): 374 (M+H)⁺, 290, 187.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0206(3R)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-isobutylazepan-3-amine

MS (ESI, Pos. 20 V): 346 (M+H)⁺, 290, 173.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0207(3R)-N-(4-azepan-1-ylpyrimidin-2-yl)-1-cyclohexylazepan-3-amine

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 346, 290, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-02084-azepan-1-yl-N-[(3R)-1-benzylpiperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 366 (M+H)⁺, 276;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-02094-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 367 (M+H)⁺, 184 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-02104-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 360 (M+H)⁺, 276, 180.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-02114-azepan-1-yl-N-[(3R)-1-isobutylpiperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 332 (M+H)⁺, 276, 166.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-02124-azepan-1-yl-N-[(3R)-1-cyclohexylpiperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 276, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-02134-azepan-1-yl-N-[1-(3,3-dimethylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 262, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02144-azepan-1-yl-N-[1-(2-methoxy-1-methylethyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 334 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-02154-azepan-1-yl-N-(1-cyclobutylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 316 (M+H)⁺, 262, 193;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-02164-azepan-1-yl-N-(1-tetrahydro-2H-thiopyran-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 362 (M+H)⁺, 262, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-02174-azepan-1-yl-N-(1-cyclopentylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 330 (M+H)⁺, 262, 193, 165.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-02184-azepan-1-yl-N-[1-(1-methylbutyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 332 (M+H)⁺, 262, 166.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-02194-azepan-1-yl-N-[1-(1,2-dimethylpropyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 332 (M+H)⁺, 262, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-02204-azepan-1-yl-N-[1-(2,2-dimethoxy-1-methylethyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 364 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-02214-azepan-1-yl-N-[1-(1,3-dimethylbutyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 346 (M+H)⁺, 262, 173.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-02224-azepan-1-yl-N-[1-(1-methylpentyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 346 (M+H)⁺, 262, 173.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-02234-azepan-1-yl-N-[1-(3,3-dimethoxy-1-methylpropyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 378 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-02244-azepan-1-yl-N-[1-(1-methylpent-4-enyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 344 (M+H)⁺, 262, 172.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-02254-azepan-1-yl-N-(1-cyclohex-2-en-1-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 342 (M+H)⁺, 262, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-02264-azepan-1-yl-N-[1-(2-methylcyclopentyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 344 (M+H)⁺, 262, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-02274-azepan-1-yl-N-[1-(3-methylcyclopentyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 344 (M+H)⁺, 262, 172.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-02284-azepan-1-yl-N-[1-(1-ethylbutyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 346 (M+H)⁺, 262, 173.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-02294-azepan-1-yl-N-[1-(2-methylcyclopent-2-en-1-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 342 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-02304-azepan-1-yl-N-[1-(1-methylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 359 (M+H)⁺, 262, 180 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 11-02314-azepan-1-yl-N-[1-(1-methylhexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 360 (M+H)⁺, 262, 180.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-02324-azepan-1-yl-N-[1-(1-ethylpentyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 360 (M+H)⁺, 262, 180.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02334-azepan-1-yl-N-[1-(2-methylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 262, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-02344-azepan-1-yl-N-[1-(3-methylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 262, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-02354-azepan-1-yl-N-[1-(4-methylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 262, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-02364-azepan-1-yl-N-[1-(3,4-dimethylcyclopentyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 262, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-02374-azepan-1-yl-N-[1-(2-methoxycyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 374 (M+H)⁺, 262; HPLC condition: A; HPLC retentiontime (min): 3.05.

Example 11-02384-azepan-1-yl-N-[1-(1-propylbutyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 360 (M+H)⁺, 262, 180.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02394-azepan-1-yl-N-(1-cycloheptylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 262, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-02404-azepan-1-yl-N-(1-tricyclo[2.2.1.0^(2,6)]hept-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 354 (M+H)⁺, 262, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-02414-azepan-1-yl-N-[1-(1-isopropylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 387 (M+H)⁺, 262, 194 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.85.

Example 11-02424-azepan-1-yl-N-[1-(1-methylheptyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 374 (M+H)⁺, 262, 187.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-02434-azepan-1-yl-N-[1-(1-cyclohexylethyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 262, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02444-azepan-1-yl-N-[1-(1-propylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 387 (M+H)⁺, 262, 194 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-02454-azepan-1-yl-N-[1-(1,4-dioxaspiro[4.5]dec-8-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 402 (M+H)⁺, 262, 193;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-02464-azepan-1-yl-N-(1-cyclooctylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02474-azepan-1-yl-N-[1-(3,5-dimethylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 262, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-02484-azepan-1-yl-N-1-[3-(diethylamino)-1-methylpropyl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 389 (M+H)⁺, 262, 195 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-02494-azepan-1-yl-N-[1-(1-ethylhexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 374 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-02504-azepan-1-yl-N-[1-(2,3-dihydro-1H-inden-2-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 378 (M+H)⁺, 262, 189.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-02514-azepan-1-yl-N-1-[4-(trifluoromethyl)cyclohexyl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 412 (M+H)⁺, 262, 206.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02524-azepan-1-yl-N-[1-(2-propylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 262, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-02534-azepan-1-yl-N-[1-(1-cyclohexylpropyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-02544-azepan-1-yl-N-[1-(1-butylpentyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 388 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-02554-azepan-1-yl-N-[1-(1-methyl-3-phenylpropyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 394 (M+H)⁺, 262, 197.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-02564-azepan-1-yl-N-(1-decahydronaphthalen-2-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 398 (M+H)⁺, 262, 199.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-02574-azepan-1-yl-N-(1-cyclodecylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 400 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-02584-azepan-1-yl-N-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 392 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02594-azepan-1-yl-N-[1-(1-pentylhexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 416 (M+H)⁺, 262, 208.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.51.

Example 11-02604-azepan-1-yl-N-[1-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 422 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-02614-azepan-1-yl-N-[1-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 422 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-02624-azepan-1-yl-N-[1-(1-benzylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 435 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-02634-azepan-1-yl-N-(1-cyclododecylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 428 (M+H)⁺, 262, 214.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.45.

Example 11-02644-azepan-1-yl-N-[1-(4-phenylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 420 (M+H)⁺, 262, 210.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-02654-azepan-1-yl-N-[1-(2-phenylcyclohexyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 420 (M+H)⁺, 262, 210.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-02664-azepan-1-yl-N-1-[1-(2-phenylethyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 449 (M+H)⁺, 262, 225 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-02674-azepan-1-yl-N-[1-(1-methyl-2,2-diphenylethyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 456 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-02684-azepan-1-yl-N-[1-(1-benzyl-2-phenylethyl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 456 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 3.36.

Example 11-02694-azepan-1-yl-N-(1-tetrahydrothien-3-ylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 362 (M+H)⁺, 276, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-02704-azepan-1-yl-N-[1-(3,3-dimethylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 276, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-02714-azepan-1-yl-N-(1-cyclobutylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 330 (M+H)⁺, 276, 193, 165.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-02724-azepan-1-yl-N-(1-tetrahydro-2H-thiopyran-4-ylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 376 (M+H)⁺, 276, 188.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-02734-azepan-1-yl-N-(1-cyclopentylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 344 (M+H)⁺, 276, 172.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-02744-azepan-1-yl-N-[1-(1-methylbutyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 346 (M+H)⁺, 276, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-02754-azepan-1-yl-N-[1-(3-methylcyclopentyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 276, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-02764-azepan-1-yl-N-[1-(1-ethylbutyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 360 (M+H)⁺, 318;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0277N-(4-azepan-1-ylpyrimidin-2-yl)-1′-methyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 373 (M+H)⁺, 276, 187 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 11-02784-azepan-1-yl-N-(1-cyclohept-2-en-1-ylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 370 (M+H)⁺, 276;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-02794-azepan-1-yl-N-[1-(1-methylhexyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 374 (M+H)⁺, 276, 187.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-02804-azepan-1-yl-N-[1-(3-methylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 276, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-02814-azepan-1-yl-N-[1-(3,4-dimethylcyclopentyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 372 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-02824-azepan-1-yl-N-(1-cycloheptylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 276, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-02834-azepan-1-yl-N-(1-tricyclo[2.2.1.0^(2,6)]hept-3-ylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 368 (M+H)⁺, 276, 184.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0284N-(4-azepan-1-ylpyrimidin-2-yl)-1′-isopropyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 401 (M+H)⁺, 276, 201 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.85.

Example 11-02854-azepan-1-yl-N-[1-(1-methylheptyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 388 (M+H)⁺, 276, 194.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-0286N-(4-azepan-1-ylpyrimidin-2-yl)-1′-propyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 401 (M+H)⁺, 276, 201 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-02874-azepan-1-yl-N-[1-(1,4-dioxaspiro[4.5]dec-8-yl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 416 (M+H)⁺, 276, 208.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-02884-azepan-1-yl-N-(1-cyclooctylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 276, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-02894-azepan-1-yl-N-[1-(3,5-dimethylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 276, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-02904-azepan-1-yl-N-1-[3-(diethylamino)-1-methylpropyl]piperidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 403 (M+H)⁺, 276, 202 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-02914-azepan-1-yl-N-[1-(1-ethylhexyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 388 (M+H)⁺, 276, 194.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-02924-azepan-1-yl-N-[1-(2,3-dihydro-1H-inden-2-yl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 392 (M+H)⁺, 276, 196.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-02934-azepan-1-yl-N-1-[4-(trifluoromethyl)cyclohexyl]piperidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 426 (M+H)⁺, 276, 213.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-02944-azepan-1-yl-N-[1-(1-methyl-3-phenylpropyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 408 (M+H)⁺, 276, 204.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-02954-azepan-1-yl-N-(1-decahydronaphthalen-2-ylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 412 (M+H)⁺, 276, 206.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-02964-azepan-1-yl-N-[1-(1,2,3,4-tetrahydronaphthalen-2-yl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 406 (M+H)⁺, 276;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-02974-azepan-1-yl-N-[1-(1-pentylhexyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 430 (M+H)⁺, 276, 215.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.49.

Example 11-02984-azepan-1-yl-N-[1-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 436 (M+H)⁺, 276;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0299N-(4-azepan-1-ylpyrimidin-2-yl)-1′-benzyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 449 (M+H)⁺, 276, 225 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-03004-azepan-1-yl-N-[1-(4-phenylcyclohexyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 434 (M+H)⁺, 276, 217.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0301N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-phenylethyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 276, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0302N-(4-azepan-1-ylpyrimidin-2-yl)-1′-ethyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 387 (M+H)⁺, 276, 194 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 11-0303N-(4-azepan-1-ylpyrimidin-2-yl)-1′-benzyl-3′-methyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-03044-azepan-1-yl-N-(1-cyclopent-3-en-1-ylpiperidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 342 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-03054-azepan-1-yl-N-[1-(1-propylheptyl)piperidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 416 (M+H)⁺, 276, 208.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-03064-azepan-1-yl-N-1-[2-(benzyloxy)-1-methylethyl]piperidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 424 (M+H)⁺, 334;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0307N-(4-azepan-1-ylpyrimidin-2-yl)-1′-isobutyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 276, 208 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-0308N-(4-azepan-1-ylpyrimidin-2-yl)-1-tetrahydrothien-3-ylazepan-3-amine

MS (ESI, Pos.20V): 376 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0309N-(4-azepan-1-ylpyrimidin-2-yl)-1-(3,3-dimethylcyclohexyl)azepan-3-amine

MS (ESI, Pos.20V): 400 (M+H)⁺, 332, 200.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0310N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2-methoxy-1-methylethyl)azepan-3-amine

MS (ESI, Pos.20V): 362 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0311N-(4-azepan-1-ylpyrimidin-2-yl)-1-cyclobutylazepan-3-amine

MS (ESI, Pos.20V): 344 (M+H)⁺, 290, 172.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0312N-(4-azepan-1-ylpyrimidin-2-yl)-1-tetrahydro-2H-thiopyran-4-ylazepan-3-amine

MS (ESI, Pos.20V): 390 (M+H)⁺, 290, 195.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0313N-(4-azepan-1-ylpyrimidin-2-yl)-1-cyclopentylazepan-3-amine

MS (ESI, Pos.20V): 358 (M+H)⁺, 290, 179.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0314N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-methylbutyl)azepan-3-amine

MS (ESI, Pos.20V): 360 (M+H)⁺, 290, 180.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0315N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2,2-dimethoxy-1-methylethyl)azepan-3-amine

MS (ESI, Pos.20V): 392 (M+H)⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0316N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1,3-dimethylbutyl)azepan-3-amine

MS (ESI, Pos.20V): 374 (M+H)⁺, 187.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0317N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-methylpentyl)azepan-3-amine

MS (ESI, Pos.20V): 374 (M+H)⁺, 187.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0318N-(4-azepan-1-ylpyrimidin-2-yl)-1-(3,3-dimethoxy-1-methylpropyl)azepan-3-amine

MS (ESI, Pos.20V): 406 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0319N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-methylpent-4-enyl)azepan-3-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0320N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2-methylcyclopentyl)azepan-3-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 290, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0321N-(4-azepan-1-ylpyrimidin-2-yl)-1-(3-methylcyclopentyl)azepan-3-amine

MS (ESI, Pos.20V): 372 (M+H)⁺, 290, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0322N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-methylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 387 (M+H)⁺, 290, 194 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-0323N-(4-azepan-1-ylpyrimidin-2-yl)-1-cyclohept-2-en-1-ylazepan-3-amine

MS (ESI, Pos.20V): 384 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0324N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-methylhexyl)azepan-3-amine

MS (ESI, Pos.20V): 388 (M+H)⁺, 290, 194.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0325N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-ethylpentyl)azepan-3-amine

MS (ESI, Pos.20V): 388 (M+H)⁺, 290, 194.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0326N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2-methylcyclohexyl)azepan-3-amine

MS (ESI, Pos.20V): 386 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0327N-(4-azepan-1-ylpyrimidin-2-yl)-1-(3-methylcyclohexyl)azepan-3-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 290, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0328N-(4-azepan-1-ylpyrimidin-2-yl)-1-(4-methylcyclohexyl)azepan-3-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 290, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0329N-(4-azepan-1-ylpyrimidin-2-yl)-1-(3,4-dimethylcyclopentyl)azepan-3-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 290, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0330N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2-methoxycyclohexyl)azepan-3-amine

MS (ESI, Pos.20V): 402 (M+H)⁺, 290, 201.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0331N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-propylbutyl)azepan-3-amine

MS (ESI, Pos.20V): 388 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0332N-(4-azepan-1-ylpyrimidin-2-yl)-1-cycloheptylazepan-3-amine

MS (ESI, Pos.20V): 386 (M+H)⁺, 290, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0333N-(4-azepan-1-ylpyrimidin-2-yl)-1-tricyclo[2.2.1.0^(2,6)]hept-3-ylazepan-3-amine

MS (ESI, Pos.20V): 382 (M+H)⁺, 290, 191.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0334N-(4-azepan-1-ylpyrimidin-2-yl)-1-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]azepan-3-amineExample 11-0335N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-isopropylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 290, 208 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-0336N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-methylheptyl)azepan-3-amine

MS (ESI, Pos.20V): 402 (M+H)⁺, 290, 201.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-0337N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-cyclohexylethyl)azepan-3-amine

MS (ESI, Pos.20V): 400 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0338N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-propylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 290, 208 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-0339N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1,4-dioxaspiro[4.5]dec-8-yl)azepan-3-amine

MS (ESI, Pos.20V): 430 (M+H)⁺, 215.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0340N-(4-azepan-1-ylpyrimidin-2-yl)-1-cyclooctylazepan-3-amine

MS (ESI, Pos.20V): 400 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0341N-(4-azepan-1-ylpyrimidin-2-yl)-1-[3-(diethylamino)-1-methylpropyl]azepan-3-amine

MS (ESI, Pos.20V): 417 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-0342N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-ethylhexyl)azepan-3-amine

MS (ESI, Pos.20V): 402 (M+H)⁺, 290, 201.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0343N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2,3-dihydro-1H-inden-2-yl)azepan-3-amine

MS (ESI, Pos.20V): 406 (M+H)⁺, 203.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0344N-(4-azepan-1-ylpyrimidin-2-yl)-1-[4-(trifluoromethyl)cyclohexyl]azepan-3-amine

MS (ESI, Pos.20V): 440 (M+H)⁺, 220.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0345N-(4-azepan-1-ylpyrimidin-2-yl)-1-(2-propylcyclohexyl)azepan-3-amine

MS (ESI, Pos.20V): 414 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0346N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-methyl-3-phenylpropyl)azepan-3-amine

MS (ESI, Pos.20V): 422 (M+H)⁺, 290, 211.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0347N-(4-azepan-1-ylpyrimidin-2-yl)-1-decahydronaphthalen-2-ylazepan-3-amine

MS (ESI, Pos.20V): 426 (M+H)⁺, 213.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-0348N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1,2,3,4-tetrahydronaphthalen-2-yl)azepan-3-amine

MS (ESI, Pos.20V): 420 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0349N-(4-azepan-1-ylpyrimidin-2-yl)-1-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)azepan-3-amine

MS (ESI, Pos.20V): 450 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0350N-(4-azepan-1-ylpyrimidin-2-yl)-1-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)azepan-3-amine

MS (ESI, Pos.20V): 450 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0351N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-benzylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 290, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0352N-(4-azepan-1-ylpyrimidin-2-yl)-1-cyclododecylazepan-3-amine

MS (ESI, Pos.20V): 456 (M+H)⁺, 290, 228.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.47.

Example 11-0353N-(4-azepan-1-ylpyrimidin-2-yl)-1-(4-phenylcyclohexyl)azepan-3-amine

MS (ESI, Pos.20V): 448 (M+H)⁺, 224.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0354N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-phenylethyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0355N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-ethylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 401 (M+H)⁺, 290, 201 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-0356N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-benzyl-3-methylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 239 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0357N-(4-azepan-1-ylpyrimidin-2-yl)-1-[2-(benzyloxy)-1-methylethyl]azepan-3-amine

MS (ESI, Pos.20V): 438 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0358N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-isobutylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 290, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-03591-(2-adamantyl)-N-(4-azepan-1-ylpyrimidin-2-yl)azepan-3-amine

MS (ESI, Pos.20V): 424 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-03604-azepan-1-yl-N-[1-(1-isobutyrylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 345, 208 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-03614-azepan-1-yl-N-[1-(1-butyrylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 345, 262, 208 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-03624-azepan-1-yl-N-1-[1-(3-methylbenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 345, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0363N-[1-(1-acetylpiperidin-3-yl)pyrrolidin-3-yl]-4-azepan-1-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 387 (M+H)⁺, 345, 194 (M+2H)²⁺; HPLC condition: A;HPLC retention time (min): 2.90.

Example 11-03644-azepan-1-yl-N-1-[1-(4-fluorobenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 345, 234 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-03654-azepan-1-yl-N-1-[1-(4-methylbenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 345, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-03664-azepan-1-yl-N-[1-(1-heptanoylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 345, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-03674-azepan-1-yl-N-1-[1-(2-methoxybenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 345, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-03684-azepan-1-yl-N-1-[1-(2-methylbenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-03694-azepan-1-yl-N-[1-(1-hexanoylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345, 222 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-03704-azepan-1-yl-N-1-[1-(phenylacetyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-03714-azepan-1-yl-N-1-[1-(4-methoxybenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 345, 135;

HPLC condition: A; HPLC retention time (min): 3.06.

Example 11-03724-azepan-1-yl-N-(1-1-[(2E)-3-phenylprop-2-enoyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 949 (2M+H)⁺, 475 (M+H)⁺, 131;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-03734-azepan-1-yl-N-[1-(1-propionylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 401 (M+H)⁺, 262, 201 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2, 94.

Example 11-03744-azepan-1-yl-N-1-[1-(cyclopropylcarbonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 413 (M+H)⁺, 345, 207 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-03754-azepan-1-yl-N-1-[1-(2-chlorobenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 345, 242 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-03764-azepan-1-yl-N-1-[1-(cyclohexylcarbonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 345, 228 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-03774-azepan-1-yl-N-1-[1-(2-furoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 439 (M+H)⁺, 262, 220 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-03784-azepan-1-yl-N-[1-(1-pentanoylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 345, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-03794-azepan-1-yl-N-1-[1-(phenoxyacetyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-03804-azepan-1-yl-N-[1-(1-octanoylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 345, 236 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-03814-azepan-1-yl-N-1-[1-(3-phenylpropanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 345, 239 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-03824-azepan-1-yl-N-(1-1-[2-(trifluoromethyl)benzoyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 517 (M+H)⁺, 259 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-03834-azepan-1-yl-N-1-[1-(2-naphthoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 997 (2M+H)⁺, 499 (M+H)⁺, 155;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-03844-azepan-1-yl-N-1-[1-(thien-2-ylacetyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 235 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-03854-azepan-1-yl-N-1-[1-(3,3-dimethylbutanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345, 222 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-03864-azepan-1-yl-N-1-[1-(3-methoxybenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 345, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-03874-azepan-1-yl-N-1-[1-(2-ethylhexanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 345, 236 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-03884-azepan-1-yl-N-1-[1-(3-fluorobenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 345, 234 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-03894-azepan-1-yl-N-1-[1-(3-chlorobenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 345, 242 (M+2H)²⁺, 139;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-03904-azepan-1-yl-N-1-[1-(4-tert-butylbenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 505 (M+H)⁺, 345, 161;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-03914-azepan-1-yl-N-1-[1-(thien-2-ylcarbonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 345, 228 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-03924-azepan-1-yl-N-(1-1-[(4-chlorophenyl)acetyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 499, 497 (M+H)⁺, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-03934-azepan-1-yl-N-1-[1-(3-methylbutanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 345, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-03944-azepan-1-yl-N-(1-1-[4-(trifluoromethyl)benzoyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 517 (M+H)⁺, 259 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-03954-azepan-1-yl-N-[1-(1-benzoylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 449 (M+H)⁺, 345, 225 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-03964-azepan-1-yl-N-1-[1-(2-fluorobenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 345, 234 (M+2H)²⁺, 123;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-03974-azepan-1-yl-N-1-[1-(diphenylacetyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 539 (M+H)⁺, 345, 270 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-03984-azepan-1-yl-N-1-[1-(2-phenoxypropanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 247(M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-03994-azepan-1-yl-N-1-[1-(2-methylpentanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345, 222 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-04004-azepan-1-yl-N-1-[1-(methoxyacetyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 417 (M+H)⁺, 345, 262, 209 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-0401 ethyl4-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-4-oxobutanoate

MS (ESI, Pos.20V): 473 (M+H)⁺, 237 (M+2H)²⁺, 214;

HPLC condition: A;

HPLC retention time (min): 3.01.

Example 11-04024-azepan-1-yl-N-1-[1-(3-cyclopentylpropanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 345, 235 (M+2H)²⁺;

HPLC condition: A;

HPLC retention time (min): 3.25.

Example 11-04034-azepan-1-yl-N-1-[1-(2-propylpentanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 345, 236 (M+2H)²⁺;

HPLC condition: A;

HPLC retention time (min): 3.27.

Example 11-0404 Methyl5-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 473 (M+H)⁺, 237 (M+2H)²⁺, 221, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-04054-azepan-1-yl-N-(1-1-[(4-chlorophenoxy)acetyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 515, 513 (M+H)⁺, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-04074-azepan-1-yl-N-1-[1-(cyclopentylacetyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 345, 228 (M+2H)²⁺, 173;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-04084-azepan-1-yl-N-1-[1-(cyclopentylcarbonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 441 (M+H)⁺, 345, 221 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-04094-azepan-1-yl-N-1-[1-(mesitylcarbonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 345, 147;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-04104-azepan-1-yl-N-(1-1-[(3-methoxyphenyl)acetyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 247 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0411 ethyl3-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-3-oxopropanoate

MS (ESI, Pos.20V): 459 (M+H)⁺, 262, 230 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-04124-azepan-1-yl-N-1-[1-(4-butoxybenzoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 345, 177;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-04134-azepan-1-yl-N-(1-1-[(benzyloxy)acetyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 403;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-04144-azepan-1-yl-N-1-[1-(2-methylbutanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 345, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-04154-azepan-1-yl-N-(1-1-[(4-methoxyphenyl)acetyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 345, 247 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0416 ethyl5-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 393, 244 (M+2H)²⁺, 221;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-04174-azepan-1-yl-N-1-[1-(cyclobutylcarbonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 427 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04184-azepan-1-yl-N-1-[1-(2-ethylbutanoyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345, 222 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-04194-azepan-1-yl-N-(1-1-[4-(trifluoromethoxy)benzoyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 533 (M+H)⁺, 345, 267 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-04204-azepan-1-yl-N-1-[1-(methylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 423 (M+H)⁺, 345, 262 (M+2H)²⁺, 212;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-04214-azepan-1-yl-N-1-[1-(pentylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 262, 240 (M+2H)²⁺, 212;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-04224-azepan-1-yl-N-1-[1-(propylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 451 (M+H)⁺, 262, 226 (M+2H)²⁺, 190;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-04234-azepan-1-yl-N-1-[1-(isopropylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 451 (M+H)⁺, 345, 262, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04244-azepan-1-yl-N-(1-piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 345 (M+H)⁺, 262;

HPLC condition: A; HPLC retention time (min): 2.80.

Example 11-04254-azepan-1-yl-N-1-[1-(butylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 465 (M+H)⁺, 262, 233(M+2H)²⁺, 204;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-04264-azepan-1-yl-N-1-[1-(phenylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 262, 243 (M+2H)²⁺, 224;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-04274-azepan-1-yl-N-[1-(1-[4-(trifluoromethyl)phenyl]sulfonylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 553 (M+H)⁺, 277(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-04284-azepan-1-yl-N-(1-1-[(4-methoxyphenyl)sulfonyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 515 (M+H)⁺, 345, 258 (M+2H)²⁺, 171;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-04294-azepan-1-yl-N-1-[1-(benzylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 345, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-04304-azepan-1-yl-N-(1-1-[(4-methylphenyl)sulfonyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 262, 250 (M+2H)²⁺, 238; HPLC condition:A; HPLC retention time (min): 3.20.

Example 11-04314-azepan-1-yl-N-(1-1-[(3-methylphenyl)sulfonyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 262, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-04324-azepan-1-yl-N-(1-1-[(2-methylphenyl)sulfonyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 262, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-04334-azepan-1-yl-N-[1-(1-[4-(trifluoromethoxy)phenyl]sulfonylpiperidin-3-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 569 (M+H)⁺, 308, 285 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-04344-azepan-1-yl-N-(1-1-[(4-butoxyphenyl)sulfonyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 557 (M+H)⁺, 345, 279 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.44.

Example 11-04354-azepan-1-yl-N-(1-1-[(4-tert-butylphenyl)sulfonyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 541 (M+H)⁺, 271 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.40.

Example 11-04364-azepan-1-yl-N-(1-1-[(4-nitrophenyl)sulfonyl]piperidin-3-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 530 (M+H)⁺, 265 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-04374-[(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)sulfonyl]benzonitrile

MS (ESI, Pos.20V): 510 (M+H)⁺, 255(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-04384-azepan-1-yl-N-1-[1-(2-naphthylsulfonyl)piperidin-3-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 535 (M+H)⁺, 268 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-04394-azepan-1-yl-N-[1-(1-isobutyrylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-04404-azepan-1-yl-N-[1-(1-butyrylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-04414-azepan-1-yl-N-1-[1-(3-methylbenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 345, 119;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0442N-[1-(1-acetylpiperidin-4-yl)pyrrolidin-3-yl]-4-azepan-1-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 387 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-04434-azepan-1-yl-N-1-[1-(4-fluorobenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 345, 193, 123;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-04444-azepan-1-yl-N-1-[1-(4-methylbenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 345, 119;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-04454-azepan-1-yl-N-[1-(1-heptanoylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 345, 229 (M+2H)²⁺, 173;

HPLC condition: A; HPLC retention time (min): 3.2.

Example 11-04464-azepan-1-yl-N-1-[1-(2-methoxybenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 345, 193, 135; HPLC condition: A; HPLCretention time (min): 3.03.

Example 11-04474-azepan-1-yl-N-1-[1-(2-methylbenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 345, 119; HPLC condition: A; HPLCretention time (min): 3.07.

Example 11-04484-azepan-1-yl-N-[1-(1-hexanoylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345, 173;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-04494-azepan-1-yl-N-1-[1-(phenylacetyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-04504-azepan-1-yl-N-1-[1-(4-methoxybenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 345, 193, 135;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04514-azepan-1-yl-N-(1-1-[(2E)-3-phenylprop-2-enoyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 949 (2M+H)⁺, 475 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-04524-azepan-1-yl-N-[1-(1-propionylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 401 (M+H)⁺, 345, 173;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-04534-azepan-1-yl-N-1-[1-(cyclopropylcarbonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 413 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-04544-azepan-1-yl-N-1-[1-(2-chlorobenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 485, 483 (M+H)⁺, 345, 139;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-04554-azepan-1-yl-N-1-[1-(cyclohexylcarbonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-04564-azepan-1-yl-N-1-[1-(2-furoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 439 (M+H)⁺, 220 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-04574-azepan-1-yl-N-[1-(1-pentanoylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-04584-azepan-1-yl-N-1-[1-(phenoxyacetyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 429, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-04594-azepan-1-yl-N-[1-(1-octanoylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 345, 236 (M+2H)²⁺, 173;

HPLC condition: A; HPLC retention time (min): 3.28.

Example 11-04604-azepan-1-yl-N-1-[1-(3-phenylpropanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 345, 239 (M+2H)²⁺, 173;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-04614-azepan-1-yl-N-(1-1-[2-(trifluoromethyl)benzoyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 517 (M+H)⁺, 259 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-04624-azepan-1-yl-N-1-[1-(2-naphthoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 997 (2M+H)⁺, 499 (M+H)⁺, 155;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-04634-azepan-1-yl-N-1-[1-(thien-2-ylacetyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 235 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-04644-azepan-1-yl-N-1-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345, 173;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-04654-azepan-1-yl-N-1-[1-(3-methoxybenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 345, 135;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-04664-azepan-1-yl-N-1-[1-(2-ethylhexanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-04674-azepan-1-yl-N-1-[1-(3-fluorobenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 345, 234 (M+2H)²⁺, 123;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-04684-azepan-1-yl-N-1-[1-(3-chlorobenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 345, 138;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-04694-azepan-1-yl-N-1-[1-(4-tert-butylbenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 505 (M+H)⁺, 345, 161;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-04704-azepan-1-yl-N-1-[1-(thien-2-ylcarbonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04714-azepan-1-yl-N-(1-1-[(4-chlorophenyl)acetyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 499, 497 (M+H)⁺, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-04724-azepan-1-yl-N-1-[1-(3-methylbutanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04734-azepan-1-yl-N-(1-1-[4-(trifluoromethyl)benzoyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 517 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-04744-azepan-1-yl-N-[1-(1-benzoylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 449 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04754-azepan-1-yl-N-1-[1-(2-fluorobenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 345, 234 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04764-azepan-1-yl-N-1-[1-(diphenylacetyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 539 (M+H)⁺, 345, 167;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-04774-azepan-1-yl-N-1-[1-(2-phenoxypropanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 345, 247 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-04784-azepan-1-yl-N-1-[1-(2-methylpentanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-04794-azepan-1-yl-N-1-[1-(methoxyacetyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 417 (M+H)⁺, 345, 262 (M+2H)²⁺, 209;

HPLC condition: A; HPLC retention time (min): 2.86.

Example 11-0480 ethyl4-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-4-oxobutanoate

MS (ESI, Pos.20V): 473 (M+H)⁺, 214;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-04814-azepan-1-yl-N-1-[1-(3-cyclopentylpropanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 345, 235 (M+2H)²⁺, 173;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-04824-azepan-1-yl-N-1-[1-(2-propylpentanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0483 methyl5-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 473 (M+H)⁺, 221; HPLC condition: A; HPLC retentiontime (min): 3.00.

Example 11-04844-azepan-1-yl-N-(1-1-[(4-chlorophenoxy)acetyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-04864-azepan-1-yl-N-1-[1-(cyclopentylacetyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 345, 173;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-04874-azepan-1-yl-N-1-[1-(cyclopentylcarbonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 441 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-04884-azepan-1-yl-N-1-[1-(mesitylcarbonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 345, 147;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-04894-azepan-1-yl-N-(1-1-[(3-methoxyphenyl)acetyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 247 (M+2H)²⁺, 173;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0490 ethyl3-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-3-oxopropanoate

MS (ESI, Pos.20V): 459 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-04914-azepan-1-yl-N-1-[1-(4-butoxybenzoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 345, 177;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-04924-azepan-1-yl-N-(1-1-[(benzyloxy)acetyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 403;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-04934-azepan-1-yl-N-1-[1-(2-methylbutanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-04944-azepan-1-yl-N-(1-1-[(4-methoxyphenyl)acetyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 247 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0495 ethyl5-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 393, 221;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-04964-azepan-1-yl-N-1-[1-(cyclobutylcarbonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 427 (M+H)⁺, 345, 193;

HPLC condition: A; HPLC retention time (min): 3.02.

Example 11-04974-azepan-1-yl-N-1-[1-(2-ethylbutanoyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-04984-azepan-1-yl-N-(1-1-[4-(trifluoromethoxy)benzoyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 533 (M+H)⁺, 189;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-04994-azepan-1-yl-N-1-[1-(methylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 423 (M+H)⁺, 262 (M+2H)²⁺, 212;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-05004-azepan-1-yl-N-1-[1-(pentylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 957 (2M+H)⁺, 479 (M+H)⁺, 240(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-05014-azepan-1-yl-N-1-[1-(propylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 901 (2M+H)⁺, 451 (M+H)⁺, 226 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-05024-azepan-1-yl-N-1-[1-(isopropylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 901 (2M+H)⁺, 451 (M+H)⁺, 226 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-05034-azepan-1-yl-N-(1-piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 345 (M+H)⁺, 262, 173 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.79.

Example 11-05044-azepan-1-yl-N-1-[1-(butylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 929 (2M+H)⁺, 465 (M+H)⁺, 233 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-05054-azepan-1-yl-N-1-[1-(phenylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 969 (2M+H)⁺, 485 (M+H)⁺, 243 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.13.

Example 11-05064-azepan-1-yl-N-(1-1-[(4-chlorophenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 521, 519 (M+H)⁺, 260(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-05074-azepan-1-yl-N-[1-(1-[4-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 553 (M+H)⁺, 277 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-05084-azepan-1-yl-N-(1-1-[(4-methoxyphenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 515 (M+H)⁺, 345, 258 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-05094-azepan-1-yl-N-1-[1-(benzylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 997 (2M+H)⁺, 499 (M+H)⁺, 345;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-05104-azepan-1-yl-N-(1-1-[(4-methylphenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 997 (2M+H)⁺, 499 (M+H)⁺, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-05114-azepan-1-yl-N-(1-1-[(3-methylphenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 997 (2M+H)⁺, 499 (M+H)⁺, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-05124-azepan-1-yl-N-(1-1-[(2-methylphenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 997 (2M+H)⁺, 499 (M+H)⁺, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-05134-azepan-1-yl-N-[1-(1-[4-(trifluoromethoxy)phenyl]sulfonylpiperidin-4-yl)pyrrolidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos.20V): 569 (M+H)⁺, 285 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-05144-azepan-1-yl-N-(1-1-[(4-butoxyphenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 557 (M+H)⁺, 345, 279 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-05154-azepan-1-yl-N-(1-1-[(4-tert-butylphenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 541 (M+H)⁺, 271 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-05164-azepan-1-yl-N-(1-1-[(4-nitrophenyl)sulfonyl]piperidin-4-ylpyrrolidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos.20V): 530 (M+H)⁺, 278;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-05174-[(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]pyrrolidin-1-ylpiperidin-1-yl)sulfonyl]benzonitrile

MS (ESI, Pos.20V): 510 (M+H)⁺, 255.5 (M+2H)²⁺, 186; HPLC condition: A;HPLC retention time (min): 3.18.

Example 11-05184-azepan-1-yl-N-1-[1-(2-naphthylsulfonyl)piperidin-4-yl]pyrrolidin-3-ylpyrimidin-2-amine

MS (ESI, Pos.20V): 535 (M+H)⁺, 268(M+2H)²⁺; HPLC condition: A; HPLCretention time (min): 3.31.

Example 11-0519N-(4-azepan-1-ylpyrimidin-2-yl)-1′-isobutyryl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 359, 276, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0520N-(4-azepan-1-ylpyrimidin-2-yl)-1′-butyryl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 359, 276, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0521N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-methylbenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 359, 239 (M+2H)²⁺, 119; HPLC condition:A; HPLC retention time (min): 3.11.

Example 11-05221′-acetyl-N-(4-azepan-1-ylpyrimidin-2-yl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 401 (M+H)⁺, 359, 276, 201 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-0523N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-fluorobenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 481 (M+H)⁺, 359, 241 (M+2H)²⁺, 123;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0524N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-methylbenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 359, 239 (M+2H)²⁺, 119;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0525N-(4-azepan-1-ylpyrimidin-2-yl)-1′-heptanoyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 359, 236 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0526N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methoxybenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 359, 247 (M+2H)²⁺, 135;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0527N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methylbenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 359, 239 (M+2H)²⁺, 119;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0528N-(4-azepan-1-ylpyrimidin-2-yl)-1′-hexanoyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359, 276, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0529N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(phenylacetyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 239 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0530N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-methoxybenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 359, 247 (M+2H)²⁺, 135;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0531N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(2E)-3-phenylprop-2-enoyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 489 (M+H)⁺, 359, 245 (M+2H)²⁺, 204;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0532N-(4-azepan-1-ylpyrimidin-2-yl)-1′-propionyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 359, 276, 208 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-0533N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopropylcarbonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 427 (M+H)⁺, 359, 276, 214 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0534N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-chlorobenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 499, 497 (M+H)⁺, 359, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0535N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclohexylcarbonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 359, 235 (M+2H)²⁺, 111;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0536N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-furoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 453 (M+H)⁺, 276, 227 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0537N-(4-azepan-1-ylpyrimidin-2-yl)-1′-pentanoyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 359, 222(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0538N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(phenoxyacetyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 276, 247 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0539N-(4-azepan-1-ylpyrimidin-2-yl)-1′-octanoyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 359, 243 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-0540N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-phenylpropanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 359, 246 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0541N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[2-(trifluoromethyl)benzoyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 531 (M+H)⁺, 266 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0542N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-naphthoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 359, 257 (M+2H)²⁺, 155;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0543N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(thien-2-ylacetyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 276, 242 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0544N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3,3-dimethylbutanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0545N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-methoxybenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 359, 247 (M+2H)²⁺, 135;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0546N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-ethylhexanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 359, 243 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0547N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-fluorobenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 481 (M+H)⁺, 359, 241 (M+2H)²⁺, 123;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0548N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-chlorobenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 499, 497 (M+H)⁺, 359, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0549N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-tert-butylbenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 519 (M+H)⁺, 359, 260 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0550N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(thien-2-ylcarbonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 359, 235 (M+2H)²⁺, 111;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0551N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-chlorophenyl)acetyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513, 511 (M+H)⁺, 256 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0552N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-methylbutanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 359, 222 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0553N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethyl)benzoyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 531 (M+H)⁺, 266 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0554N-(4-azepan-1-ylpyrimidin-2-yl)-1′-benzoyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 359, 232 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0555N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-fluorobenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 481 (M+H)⁺, 359, 241 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0556N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(diphenylacetyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 553 (M+H)⁺, 359, 277 (M+2H)²⁺, 167;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0557N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-phenoxypropanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 254 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0558N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methylpentanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0559N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(methoxyacetyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 431 (M+H)⁺, 359, 216 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-0560 ethyl4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,3′-bipiperidin-1′-yl-4-oxobutanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 359, 244 (M+2H)²⁺, 211;

HPLC condition: A; HPLC retention time (min): 3.02.

Example 11-0561N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-cyclopentylpropanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 359, 242 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0562N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-propylpentanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 359, 243 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0563 methyl5-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,3′-bipiperidin-1′-yl-5-oxopentanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 228;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0564N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-chlorophenoxy)acetyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 529, 527 (M+H)⁺, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0566N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopentylacetyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 359, 235 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0567N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopentylcarbonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 359, 228 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0568N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(mesitylcarbonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 505 (M+H)⁺, 359, 147;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0569N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(3-methoxyphenyl)acetyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 359, 254 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0570 ethyl3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,3′-bipiperidin-1′-yl-3-oxopropanoate

MS (ESI, Pos.20V): 473 (M+H)⁺, 276, 237 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0571N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-butoxybenzoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 535 (M+H)⁺, 359, 177;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-0572N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(benzyloxy)acetyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 417;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0573N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methylbutanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 465 (M+Na)+, 443 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0574N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-methoxyphenyl)acetyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 359, 254(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0575 ethyl5-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,3′-bipiperidin-1′-yl-5-oxopentanoate

MS (ESI, Pos.20V): 501 (M+H)⁺, 228;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0576N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclobutylcarbonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 441 (M+H)⁺, 359, 221 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0577N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-ethylbutanoyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0578N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethoxy)benzoyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 547 (M+H)⁺, 359, 274 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0579N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(methylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 437 (M+H)⁺, 359, 276;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-0580N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(pentylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 276, 247 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0581N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(propylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 465 (M+H)⁺, 276, 233 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0582N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(isopropylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 465 (M+H)⁺, 359, 276, 233 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0583 N-(4-azepan-1-ylpyrimidin-2-yl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 359 (M+H)⁺, 276;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 11-0584N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(butylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 276, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0585N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(phenylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 276, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0586N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-chlorophenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 535, 533 (M+H)⁺, 267 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0587N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethyl)phenyl]sulfonyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 567 (M+H)⁺, 284 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0588N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-methoxyphenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 529 (M+H)⁺, 265 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0589N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(benzylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 359, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0590N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-methylphenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 276, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0591N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(3-methylphenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 276, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0592N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(2-methylphenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 276, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0593N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethoxy)phenyl]sulfonyl-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 583 (M+H)⁺, 292 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-0594N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-butoxyphenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 571 (M+H)⁺, 286 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-0595N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-tert-butylphenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 555 (M+H)⁺, 278 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.38.

Example 11-0596N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-nitrophenyl)sulfonyl]-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 544 (M+H)⁺, 272.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-05974-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,3′-bipiperidin-1′-ylsulfonyl)benzonitrile

MS (ESI, Pos.20V): 524 (M+H)⁺, 262.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0598N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-naphthylsulfonyl)-1,3′-bipiperidin-3-amine

MS (ESI, Pos.20V): 549 (M+H)⁺, 275 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-0599N-(4-azepan-1-ylpyrimidin-2-yl)-1′-isobutyryl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0600N-(4-azepan-1-ylpyrimidin-2-yl)-1′-butyryl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 359, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-0601N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-methylbenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 359, 119;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-06021′-acetyl-N-(4-azepan-1-ylpyrimidin-2-yl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 401 (M+H)⁺, 359, 276, 201 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-0603N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-fluorobenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 481 (M+H)⁺, 359, 123;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0604N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-methylbenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 359, 119;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0605N-(4-azepan-1-ylpyrimidin-2-yl)-1′-heptanoyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 236 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0606N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methoxybenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 359, 193, 135;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0607N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methylbenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 359, 193;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0608N-(4-azepan-1-ylpyrimidin-2-yl)-1′-hexanoyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359, 229 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0609N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(phenylacetyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 359, 239 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0610N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-methoxybenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 359, 193, 135;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0611N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(2E)-3-phenylprop-2-enoyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 977 (2M+H)⁺, 489 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0612N-(4-azepan-1-ylpyrimidin-2-yl)-1′-propionyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 359, 180;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-0613N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopropylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 427 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-0614N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-chlorobenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 499, 497 (M+H)⁺, 359, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0615N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclohexylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0616N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-furoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 453 (M+H)⁺, 359, 227 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-0617N-(4-azepan-1-ylpyrimidin-2-yl)-1′-pentanoyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 359, 222 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0618N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(phenoxyacetyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 443, 247 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0619N-(4-azepan-1-ylpyrimidin-2-yl)-1′-octanoyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 359, 243 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0620N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-phenylpropanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 359, 246 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0621N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[2-(trifluoromethyl)benzoyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 531 (M+H)⁺, 359, 266 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0622N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-naphthoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 359, 155;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0623N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(thien-2-ylacetyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 242 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0624N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3,3-dimethylbutanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359, 180;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0625N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-methoxybenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 359, 193, 135;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0626N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-ethylhexanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0627N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-fluorobenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 481 (M+H)⁺, 359, 241 (M+2H)²⁺, 123;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0628N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-chlorobenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 499, 497 (M+H)⁺, 359, 249 (M+2H)²⁺, 139

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0629N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-tert-butylbenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 519 (M+H)⁺, 359, 161;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0630N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(thien-2-ylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 359, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0631N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-chlorophenyl)acetyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513, 511 (M+H)⁺, 359, 256 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0632N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-methylbutanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 359, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0633N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethyl)benzoyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 531 (M+H)⁺, 266 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0634N-(4-azepan-1-ylpyrimidin-2-yl)-1′-benzoyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 463 (M+H)⁺, 359, 193

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0635N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-fluorobenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 481 (M+H)⁺, 359, 241 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0636N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(diphenylacetyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 553 (M+H)⁺, 359, 277 (M+2H)²⁺, 167;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0637N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-phenoxypropanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 359, 254 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0638N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methylpentanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0639N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(methoxyacetyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 431 (M+H)⁺, 359, 276, 216 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-0640 ethyl4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-yl-4-oxobutanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 244 (M+2H)²⁺, 221;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0641N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(3-cyclopentylpropanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 359, 242 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0642N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-propylpentanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0643 methyl5-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-yl-5-oxopentanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 228;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-0644N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-chlorophenoxy)acetyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 529, 527 (M+H)⁺, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0646N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclopentylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 359, 193;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0647N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(mesitylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 505 (M+H)⁺, 359, 267, 147;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0648N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(3-methoxyphenyl)acetyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 359, 254 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0649 ethyl3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-yl-3-oxopropanoate

MS (ESI, Pos.20V): 473 (M+H)⁺, 359, 237 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-0650N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(4-butoxybenzoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 535 (M+H)⁺, 359, 177;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0651N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(benzyloxy)acetyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 417;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0652N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-methylbutanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 359, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0653N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-methoxyphenyl)acetyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 359, 254 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0654 ethyl5-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-yl-5-oxopentanoate

MS (ESI, Pos.20V): 501 (M+H)⁺, 251 (M+2H)²⁺, 228;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0655N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclobutylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 441 (M+H)⁺, 359, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0656N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-ethylbutanoyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0657N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethoxy)benzoyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 547 (M+H)⁺, 359, 189;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0658N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(methylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 437 (M+H)⁺, 276, 219 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-0659N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(pentylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 985 (2M+H)⁺, 493 (M+H)⁺, 247 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0660N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(propylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 929 (2M+H)⁺, 465 (M+H)⁺, 233 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0661N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(isopropylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 929 (2M+H)⁺, 465 (M+H)⁺, 233 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0662 N-(4-azepan-1-ylpyrimidin-2-yl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 359 (M+H)⁺, 276, 180 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 11-0663N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(butylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 957 (2M+H)⁺, 479 (M+H)⁺, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0664N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(phenylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 997 (2M+H)⁺, 499 (M+H)⁺, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0665N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-chlorophenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 535, 533 (M+H)⁺, 267 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0666N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethyl)phenyl]sulfonyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 567 (M+H)⁺, 284 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-0667N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-methoxyphenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 529 (M+H)⁺, 359, 265 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0668N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(benzylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 359;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0669N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-methylphenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 276, 257 (M+2H)²⁺, 238;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0670N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(3-methylphenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 276, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0671N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(2-methylphenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 276, 257 (M+2H)²⁺, 238;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0672N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[4-(trifluoromethoxy)phenyl]sulfonyl-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 583 (M+H)⁺, 292 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-0673N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-butoxyphenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 571 (M+H)⁺, 359, 286 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.38.

Example 11-0674N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-tert-butylphenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 555 (M+H)⁺, 278 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.38.

Example 11-0675N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-nitrophenyl)sulfonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 544 (M+H)⁺, 292;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-06764-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylsulfonyl)benzonitrile

MS (ESI, Pos.20V): 524 (M+H)⁺, 262.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0677N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(2-naphthylsulfonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 549 (M+H)⁺, 275 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0678N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-isobutyrylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 373, 290, 222(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0679N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-butyrylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 290, 222(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0680N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-methylbenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 373, 246 (M+2H)²⁺, 119;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-06811-(1-acetylpiperidin-3-yl)-N-(4-azepan-1-ylpyrimidin-2-yl)azepan-3-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 373, 290, 208 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-0682N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-fluorobenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 495 (M+H)⁺, 373, 248 (M+2H)²⁺, 130;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0683N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-methylbenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 373, 246 (M+2H)²⁺, 119;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0684N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-heptanoylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 290, 243 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0685N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methoxybenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 373, 254 (M+2H)²⁺, 135;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0686N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methylbenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 373, 246 (M+2H)²⁺, 119;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0687N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-hexanoylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373, 290, 236 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0688N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(phenylacetyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 290, 246 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0689N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-methoxybenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 373, 254 (M+2H)²⁺, 135;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0690N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(2E)-3-phenylprop-2-enoyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 503 (M+H)⁺, 373, 252 (M+2H)2, 131;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0691N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-propionylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 290, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0692N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclopropylcarbonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 441 (M+H)⁺, 373, 290, 221 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0693N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-chlorobenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 513, 511 (M+H)⁺, 256 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0694N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclohexylcarbonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 373, 242 (M+2H)²⁺, 111;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0695N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-furoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 290, 234 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0696N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-pentanoylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 290, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0697N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(phenoxyacetyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 507, (M+H)⁺, 457, 290, 254 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0698N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-octanoylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 373, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.36.

Example 11-0699N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-phenylpropanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 505 (M+H)⁺, 253 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0700N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[2-(trifluoromethyl)benzoyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 545 (M+H)⁺, 273 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0701N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-naphthoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 373, 264 (M+2H)²⁺, 155;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0702N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(thien-2-ylacetyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 497 (M+H)⁺, 290, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0703N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3,3-dimethylbutanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373, 236 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0704N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-methoxybenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 373, 254 (M+2H)²⁺, 135;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0705N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-ethylhexanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 373, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-0706N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-fluorobenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 495 (M+H)⁺, 290, 248 (M+2H)²⁺, 206;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0707N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-chlorobenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 513, 511 (M+H)⁺, 290, 256 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0708N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-tert-butylbenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 533 (M+H)⁺, 373, 267 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-0709N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(thien-2-ylcarbonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 373, 242 (M+2H)²⁺, 111;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0710N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-chlorophenyl)acetyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 527, 525 (M+H)⁺, 263 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0711N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-methylbutanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 373, 290, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0712N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[4-(trifluoromethyl)benzoyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 545 (M+H)⁺, 273 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0713N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-benzoylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 373, 239 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0714N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-fluorobenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 495 (M+H)⁺, 290, 248 (M+2H)²⁺, 206;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0715N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(diphenylacetyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 567 (M+H)⁺, 373, 284, (M+2H)²⁺, 167;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0716N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-phenoxypropanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 261 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0717N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methylpentanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373, 236 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0718N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(methoxyacetyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 445 (M+H)⁺, 373, 290, 223 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-0719 ethyl4-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-4-oxobutanoate

MS (ESI, Pos.20V): 501 (M+H)⁺, 251 (M+2H)²⁺, 228;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0720N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-cyclopentylpropanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 497 (M+H)⁺, 373, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0721N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-propylpentanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 373, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-0722 methyl5-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 501 (M+H)⁺, 235;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0723N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-chlorophenoxy)acetyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 543, 541 (M+H)⁺, 271 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0725N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclopentylacetyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 373, 242 (M+2H)²⁺, 111;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0726N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclopentylcarbonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 373, 235 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0727 N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(mesitylcarbonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 519 (M+H)⁺, 373, 147;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0728N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(3-methoxyphenyl)acetyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 261 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0729 ethyl3-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-3-oxopropanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 290, 244 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0730N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-butoxybenzoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 549 (M+H)⁺, 373, 177;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-0731N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(benzyloxy)acetyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 431;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0732N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methylbutanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 373, 290, 229 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0733N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-methoxyphenyl)acetyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 261 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0734 ethyl5-(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 515 (M+H)⁺, 235;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0735N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclobutylcarbonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 373, 290, 228 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0736N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-ethylbutanoyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373, 236 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0737N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[4-(trifluoromethoxy)benzoyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 561 (M+H)⁺, 373, 281 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0738N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(methylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 451 (M+H)⁺, 373, 290, 226 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0739N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(pentylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 290, 254 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0740N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(propylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 290, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0741N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(isopropylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 479 (M+H)⁺, 290, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0742N-(4-azepan-1-ylpyrimidin-2-yl)-1-piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 745 (2M+H)⁺, 373 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-0743N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(butylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 493 (M+H)⁺, 290, 247 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0744N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(phenylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 290, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0745N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-chlorophenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 549, 547 (M+H)⁺, 274 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0746N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-[4-(trifluoromethyl)phenyl]sulfonylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 581 (M+H)⁺, 291 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-0747N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-methoxyphenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 543 (M+H)⁺, 272 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0748N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(benzylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 373, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0749N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-methylphenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 290, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.21.

Example 11-0750N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(3-methylphenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 290, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0751N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(2-methylphenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 290, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0752N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-[4-(trifluoromethoxy)phenyl]sulfonylpiperidin-3-yl)azepan-3-amine

MS (ESI, Pos.20V): 597 (M+H)⁺, 299(M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.36.

Example 11-0753N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-butoxyphenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 585 (M+H)⁺, 293 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.44.

Example 11-0754N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-tert-butylphenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 569 (M+H)⁺, 285 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-0755N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-nitrophenyl)sulfonyl]piperidin-3-ylazepan-3-amine

MS (ESI, Pos.20V): 558 (M+H)⁺, 279.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-07564-[(3-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)sulfonyl]benzonitrile

MS (ESI, Pos.20V): 538 (M+H)⁺, 269.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0757N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-naphthylsulfonyl)piperidin-3-yl]azepan-3-amine

MS (ESI, Pos.20V): 563 (M+H)⁺, 282 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0758N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-isobutyrylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0759N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-butyrylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 443 (M+H)⁺, 373, 187;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0760N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-methylbenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 373, 119;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-07611-(1-acetylpiperidin-4-yl)-N-(4-azepan-1-ylpyrimidin-2-yl)azepan-3-amine

MS (ESI, Pos.20V): 415 (M+H)⁺, 373, 290, 187;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-0762N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-fluorobenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 495 (M+H)⁺, 373, 123;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0763N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-methylbenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 373, 119;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0764N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-heptanoylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 373, 243 (M+2H)²⁺, 187;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0765N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methoxybenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 373, 135; HPLC condition: A; HPLCretention time (min): 3.05.

Example 11-0766N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methylbenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 981 (2M+H)⁺, 491 (M+H)⁺, 373, 119;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0767N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-hexanoylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373, 236 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0768N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(phenylacetyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 491 (M+H)⁺, 373, 246 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0769N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-methoxybenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 373, 135;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0770N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(2E)-3-phenylprop-2-enoyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 503 (M+H)⁺, 373, 131;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0771N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-propionylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 429 (M+H)⁺, 373, 215 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-0772N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclopropylcarbonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 441 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-0773N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-chlorobenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 513, 511 (M+H)⁺, 373, 256 (M+2H)²⁺, 139;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0774N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclohexylcarbonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0775N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-furoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 467 (M+H)⁺, 234 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-0776N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-pentanoylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 373, 187;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0777N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(phenoxyacetyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 254 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0778N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-octanoylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 373, 250 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0779N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-phenylpropanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 505 (M+H)⁺, 373, 253 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0780N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[2-(trifluoromethyl)benzoyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 545 (M+H)⁺, 373, 273 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0781N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-naphthoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 373, 155;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0782N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(thien-2-ylacetyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 497 (M+H)⁺, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0783N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3,3-dimethylbutanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373, 187;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0784N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-methoxybenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 373, 135;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0785N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-ethylhexanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0786N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-fluorobenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 495 (M+H)⁺, 373, 248 (M+2H)²⁺, 123;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0787N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-chlorobenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 513, 511 (M+H)⁺, 373, 256 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0788N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-tert-butylbenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 533 (M+H)⁺, 373, 161;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0789N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(thien-2-ylcarbonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 373, 111;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0790N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-chlorophenyl)acetyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 527, 525 (M+H)⁺, 263 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0791N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-methylbutanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 373, 187;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0792N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[4-(trifluoromethyl)benzoyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 545 (M+H)⁺, 273 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.19.

Example 11-0793N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-benzoylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 477 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0794N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-fluorobenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 495 (M+H)⁺, 373, 248 (M+2H)²⁺, 123;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0795N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(diphenylacetyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 567 (M+H)⁺, 373, 284 (M+2H)²⁺, 167;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0796N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-phenoxypropanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 373, 261 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0797N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methylpentanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-0798N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(methoxyacetyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 445 (M+H)⁺, 373, 290, 223 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-0799 ethyl4-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-4-oxobutanoate

MS (ESI, Pos.20V): 501 (M+H)⁺, 251 (M+2H)²⁺, 228;

HPLC condition: A;

HPLC retention time (min): 3.01.

Example 11-0800N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(3-cyclopentylpropanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 497 (M+H)⁺, 373, 249 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0801N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-propylpentanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 499 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0802 methyl5-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 501 (M+H)⁺, 235;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-0803N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-chlorophenoxy)acetyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 543, 541 (M+H)⁺, 271 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0805N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclopentylacetyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 483 (M+H)⁺, 373, 242 (M+2H)²⁺, 187;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0806N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclopentylcarbonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 469 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0807 N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(mesitylcarbonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 519 (M+H)⁺, 373, 147;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0808N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(3-methoxyphenyl)acetyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 261 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0809 ethyl3-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-3-oxopropanoate

MS (ESI, Pos.20V): 487 (M+H)⁺, 373, 244 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0810N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(4-butoxybenzoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 549 (M+H)⁺, 373, 177;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-0811N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(benzyloxy)acetyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 431;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-0812N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-methylbutanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 457 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0813N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-methoxyphenyl)acetyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 521 (M+H)⁺, 373, 261 (M+2H)²⁺, 121;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0814 ethyl5-(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)-5-oxopentanoate

MS (ESI, Pos.20V): 515 (M+H)⁺, 235;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0815N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(cyclobutylcarbonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 455 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0816N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-ethylbutanoyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 471 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-0817N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[4-(trifluoromethoxy)benzoyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 561 (M+H)⁺, 373, 274;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0818N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(methylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 901 (2M+H)⁺, 451(M+H)⁺, 226 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-0819N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(pentylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 507 (M+H)⁺, 373, 254 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-0820N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(propylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 957 (2M+H)⁺, 479 (M+H)⁺, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-0821N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(isopropylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 957 (2M+H)⁺, 479 (M+H)⁺, 240 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0822N-(4-azepan-1-ylpyrimidin-2-yl)-1-piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 373 (M+H)⁺, 290, 187 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-0823N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(butylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 985 (2M+H)⁺, 493 (M+H)⁺, 247 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0824N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(phenylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 513 (M+H)⁺, 290, 257 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0825N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-chlorophenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 549, 547 (M+H)⁺, 274 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-0826N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-[4-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 581 (M+H)⁺, 291 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-0827N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-methoxyphenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 543 (M+H)⁺, 373, 272 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-0828N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(benzylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 373;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0829N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-methylphenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0830N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(3-methylphenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-0831N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(2-methylphenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 527 (M+H)⁺, 290, 264 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-0832N-(4-azepan-1-ylpyrimidin-2-yl)-1-(1-[4-(trifluoromethoxy)phenyl]sulfonylpiperidin-4-yl)azepan-3-amine

MS (ESI, Pos.20V): 597 (M+H)⁺, 299 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-0833N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-butoxyphenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 585 (M+H)⁺, 373, 293 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-0834N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-tert-butylphenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 569 (M+H)⁺, 285 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-0835N-(4-azepan-1-ylpyrimidin-2-yl)-1-1-[(4-nitrophenyl)sulfonyl]piperidin-4-ylazepan-3-amine

MS (ESI, Pos.20V): 558 (M+H)⁺, 279.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-08364-[(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azepan-1-ylpiperidin-1-yl)sulfonyl]benzonitrile

MS (ESI, Pos.20V): 538 (M+H)⁺, 269.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-0837N-(4-azepan-1-ylpyrimidin-2-yl)-1-[1-(2-naphthylsulfonyl)piperidin-4-yl]azepan-3-amine

MS (ESI, Pos.20V): 563 (M+H)⁺, 282 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-08384-azepan-1-yl-N-1-[(1-methyl-1H-pyrrol-2-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 341 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-08394-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazole-3-one

MS (ESI, Pos. 20 V): 895 (2M+H)⁺, 448 (M+H)⁺, 290, 201;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-08404-azepan-1-yl-N-[1-(2-furylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 328 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-08414-azepan-1-yl-N-1-[(5-methyl-2-furyl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 342 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0842[5-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)-2-furyl]methylacetate

MS (ESI, Pos. 20 V): 400 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-0843[5-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)-2-furyl]methanol

MS (ESI, Pos. 20 V): 358 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 11-08444-azepan-1-yl-N-1-[(2E)-3-(2-furyl)prop-2-enyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 354 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-0845 4-azepan-1-yl-N-(1-benzylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 338 (M+H)⁺, 290, 248, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-08464-azepan-1-yl-N-[1-(2-methoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 368 (M+H)⁺, 248, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-08474-azepan-1-yl-N-[1-(2,3-dimethoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 795 (2M+H)⁺, 398 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-08484-azepan-1-yl-N-[1-(2,4-dimethoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 795 (2M+H)⁺, 398 (M+H)⁺, 151;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-08494-azepan-1-yl-N-[1-(2,4,6-trimethoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 855 (2M+H)⁺, 428 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-08504-azepan-1-yl-N-[1-(2,5-dimethoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 795 (2M+H)⁺, 398 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0851[2-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)phenoxy]aceticacid

MS (ESI, Pos. 20 V): 412 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-08524-azepan-1-yl-N-1-[2-(trifluoromethyl)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 406 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-08534-azepan-1-yl-N-[1-(2-methylbenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 352 (M+H)⁺, 276, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-08543-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)benzonitrile

MS (ESI, Pos. 20 V): 363 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-08554-azepan-1-yl-N-[1-(3-fluorobenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 356 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-08564-azepan-1-yl-N-[1-(3-fluoro-4-methoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 771 (2M+H)⁺, 386 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-08574-azepan-1-yl-N-[1-(3-phenoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 859 (2M+H)⁺, 430 (M+H)⁺, 183;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-08584-azepan-1-yl-N-[1-(3-methoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 368 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-08594-azepan-1-yl-N-[1-(3,4-dimethoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 795 (2M+H)⁺, 398 (M+H)⁺, 248, 193;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-08604-azepan-1-yl-N-[1-(3,4,5-trimethoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 855 (2M+H)⁺, 428 (M+H)⁺, 181;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-08614-azepan-1-yl-N-1-[4-(benzyloxy)-3-methoxybenzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 947 (2M+H)⁺, 474 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-08624-azepan-1-yl-N-1-[3-(benzyloxy)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 887 (2M+H)⁺, 444 (M+H)⁺, 197;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-08633-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)phenol

MS (ESI, Pos. 20 V): 354 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-08645-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)-2-methoxyphenol

MS (ESI, Pos. 20 V): 384 (M+H)⁺, 290, 248, 137;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-08654-azepan-1-yl-N-1-[3-(trifluoromethyl)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 406 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-08664-azepan-1-yl-N-[1-(3-methylbenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 352 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-08674-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)benzonitrile

MS (ESI, Pos. 20 V): 363 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-08684-azepan-1-yl-N-[1-(4-fluorobenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 356 (M+H)⁺, 263;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-0869N-[4-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)phenyl]acetamide

MS (ESI, Pos. 20 V): 789 (2M+H)⁺, 395 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-08704-azepan-1-yl-N-1-[4-(dimethylamino)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 381 (M+H)⁺, 248, 191 (M+2H)²⁺, 134;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-08714-azepan-1-yl-N-1-[4-(diethylamino)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 817 (2M+H)⁺, 409 (M+H)⁺, 205 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.85.

Example 11-08724-azepan-1-yl-N-[1-(4-phenoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 859 (2M+H)⁺, 430 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-08734-azepan-1-yl-N-[1-(4-methoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 368 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-08744-azepan-1-yl-N-1-[4-(benzyloxy)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 887 (2M+H)⁺, 444 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-08754-azepan-1-yl-N-[1-(1H-imidazol-2-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 328 (M+H)⁺, 248, 164.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.79.

Example 11-08764-azepan-1-yl-N-[1-(1-naphthylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 775 (2M+H)⁺, 388 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-08774-azepan-1-yl-N-1-[(4-methoxy-1-naphthyl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 418 (M+H)⁺, 248, 171;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-08784-azepan-1-yl-N-1-[3,4-bis(benzyloxy)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 550 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.45.

Example 11-08794-azepan-1-yl-N-[1-(1H-pyrrol-2-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 327 (M+H)⁺, 248, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-08804-azepan-1-yl-N-[1-(thien-2-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 344 (M+H)⁺, 290, 248, 193;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-08814-azepan-1-yl-N-1-[(3-methylthien-2-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 358 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-08824-azepan-1-yl-N-1-[(4-bromothien-2-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 424, 422 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-08834-azepan-1-yl-N-1-[(5-bromothien-2-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 424, 422 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-08844-azepan-1-yl-N-[1-(1H-indol-3-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 377 (M+H)⁺, 248, 130;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-08854-azepan-1-yl-N-[1-(pyridin-4-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 339 (M+H)⁺, 262, 170 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.74.

Example 11-08864-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)phenol

MS (ESI, Pos. 20 V): 354 (M+H)⁺, 248, 193;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-08874-azepan-1-yl-N-[1-(1,1′-biphenyl-4-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 827 (2M+H)⁺, 414 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0888 methyl4-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)benzoate

MS (ESI, Pos. 20 V): 791 (2M+H)⁺, 396 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-08894-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)benzoicacid

MS (ESI, Pos. 20 V): 763 (2M+H)⁺, 382 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-08904-azepan-1-yl-N-1-[4-(trifluoromethyl)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 406 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-08914-azepan-1-yl-N-[1-(4-methylbenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 352 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-08924-azepan-1-yl-N-(1-neopentylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 318 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-08934-azepan-1-yl-N-1-[(2E)-2-methylbut-2-enyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 316 (M+H)⁺, 282;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-08944-azepan-1-yl-N-(1-isobutylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 304 (M+H)⁺, 290, 248, 193;

HPLC condition: A; HPLC retention time (min): 2.87.

Example 11-08954-azepan-1-yl-N-[1-(2-ethylhexyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 719 (2M+H)⁺, 360 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-08964-azepan-1-yl-N-1-[(2E)-3,7-dimethyloct-2,6-dienyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 384 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-08974-azepan-1-yl-N-(1-(2E)-3-[4-(dimethylamino)phenyl]prop-2-enylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 407 (M+H)⁺, 276, 204 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-08984-azepan-1-yl-N-(1-isopentylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 318 (M+H)⁺, 159.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-0899 4-azepan-1-yl-N-(1-propylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 290 (M+H)⁺, 248, 145.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-09004-azepan-1-yl-N-1-[3-(methylsulfanyl)propyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 336 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-0901 4-azepan-1-yl-N-(1-butylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 304 (M+H)⁺, 290, 248, 193;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-09024-azepan-1-yl-N-[1-(quinolin-2-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 389 (M+H)⁺, 290, 195 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.02.

Example 11-09034-azepan-1-yl-N-[1-(3-nitrobenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 765 (2M+H)⁺, 383 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09044-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)-2,6-ditert-butylphenol

MS (ESI, Pos. 20 V): 931 (2M+H)⁺, 466 (M+H)⁺, 219;

HPLC condition: A; HPLC retention time (min): 3.40.

Example 11-09054-azepan-1-yl-N-[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 791 (2M+H)⁺, 396 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-09064-azepan-1-yl-N-[1-(3-furylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 328 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-09074-azepan-1-yl-N-[1-(2,6-dimethoxybenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 795 (2M+H)⁺, 398 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09084-azepan-1-yl-N-(1-4-[3-(dimethylamino)propoxy]benzylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 439 (M+H)⁺, 354, 220 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.85.

Example 11-09094-azepan-1-yl-N-1-[(2-methyl-1H-indol-3-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 781 (2M+H)⁺, 391 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09104-azepan-1-yl-N-[1-(cyclopropylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 302 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-0911N-1-[4-(allyloxy)benzyl]azetidin-3-yl-4-azepan-1-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 787 (2M+H)⁺, 394 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09124-azepan-1-yl-N-1-[4-(octyloxy)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 931 (2M+H)⁺, 466 (M+H)⁺, 248, 144;

HPLC condition: A; HPLC retention time (min): 3.58.

Example 11-09134-azepan-1-yl-N-1-[(1-methyl-1H-indol-3-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 781 (2M+H)⁺, 391 (M+H)⁺, 248, 144;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-09144-azepan-1-yl-N-[1-(1-benzofuran-2-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 755 (2M+H)⁺, 378 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-09154-azepan-1-yl-N-1-[2-(benzyloxy)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 444 (M+H)⁺, 354, 248;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-09164-azepan-1-yl-N-1-[4-(heptyloxy)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 903 (2M+H)⁺, 452 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.51.

Example 11-09174-azepan-1-yl-N-[1-(1,3-benzodioxol-4-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 382 (M+H)⁺, 290, 248, 135;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-09184-azepan-1-yl-N-1-[(3,5,6-trimethylcyclohex-3-en-1-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 767 (2M+H)⁺, 384 (M+H)⁺, 260, 130;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-09194-azepan-1-yl-N-1-[4-(hexyloxy)-3-methoxybenzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 935 (2M+H)⁺, 468 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.38.

Example 11-09204-azepan-1-yl-N-1-[(6-chloro-1,3-benzodioxol-5-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 418, 416 (M+H)⁺, 290, 248, 169;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09214-azepan-1-yl-N-1-[(5-ethyl-2-furyl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 356 (M+H)⁺, 290, 248, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09224-azepan-1-yl-N-[1-(4-tert-butylbenzyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 787 (2M+H)⁺, 394 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-09234-azepan-1-yl-N-[1-(3,7-dimethyloct-6-enyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 771 (2M+H)⁺, 386 (M+H)⁺, 260, 130;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-09244-azepan-1-yl-N-1-[2-(tert-butylsulfanyl)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 426 (M+H)⁺, 370;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-09254-azepan-1-yl-N-1-[4-(trifluoromethoxy)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 843 (2M+H)⁺, 422 (M+H)⁺, 175;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-09264-azepan-1-yl-N-1-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 432 (M+H)⁺, 216.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-09274-azepan-1-yl-N-(1-2-[(4-chlorophenyl)sulfanyl]benzylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 482, 480 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-09284-azepan-1-yl-N-1-[(3-methyl-1-benzothien-2-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 815 (2M+H)⁺, 408 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-09294-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)-1-naphthol

MS (ESI, Pos. 20 V): 404 (M+H)⁺, 290, 157;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-09304-azepan-1-yl-N-(1-4-[2-(diethylamino)ethoxy]benzylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 453 (M+H)⁺, 227 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 11-09314-azepan-1-yl-N-(1-[(1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 763 (2M+H)⁺, 382 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-09324-azepan-1-yl-N-1-[(6-methoxy-2-naphthyl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 835 (2M+H)⁺, 418 (M+H)⁺, 171;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-09334-azepan-1-yl-N-[1-(4-[(2E)-4-methylpent-2-enyl]cyclohex-3-en-1-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 847 (2M+H)⁺, 424 (M+H)⁺, 356;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 11-09344-azepan-1-yl-N-1-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 903 (2M+H)⁺, 454, 452 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09354-azepan-1-yl-N-1-[(2-chloroquinolin-3-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 845 (2M+H)⁺, 425, 423 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0936(3a′R,5′R,6′S,6a′R)-5′-[(3-[4-(1-azepanyl)-2-pyrimidinyl]amino-1-azetidinyl)methyl]tetrahydrospiro[cyclohexane-1,2′-furo[2,3-d][1,3]dioxol]-6′-ol

MS (ESI, Pos. 20 V): 919 (2M+H)⁺, 460 (M+H)⁺, 181;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-09374-azepan-1-yl-N-[1-(1,3-thiazol-2-ylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 345 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 2.85.

Example 11-09384-azepan-1-yl-N-1-[(5-ethylthien-2-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 248, 125;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-09392-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)quinolin-8-ol

MS (ESI, Pos. 20 V): 809 (2M+H)⁺, 405 (M+H)⁺, 290, 203 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09404-azepan-1-yl-N-1-[(2-phenyl-1H-imidazol-4-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 404 (M+H)⁺, 290, 248, 157;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 11-09414-azepan-1-yl-N-[1-(5-[3,5-bis(trifluoromethyl)phenyl]-2-furylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 540 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.44.

Example 11-0942 methyl3-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)benzoate

MS (ESI, Pos. 20 V): 791 (2M+H)⁺, 396 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.02.

Example 11-09434-azepan-1-yl-N-1-[2-(benzyloxy)ethyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 382 (M+H)⁺, 292, 234;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-09444-azepan-1-yl-N-(1-[5-(4-chlorophenyl)-2-furyl]methylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 440, 438 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-09454-azepan-1-yl-N-1-[3-(5-methyl-2-furyl)butyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 384 (M+H)⁺, 248, 163;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-09464-azepan-1-yl-N-(1-[5-(3-chlorophenyl)-2-furyl]methylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 875 (2M+H)⁺, 440, 438 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-0947 methyl3-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]azetidin-1-ylmethyl)-1H-indole-6-carboxylate

MS (ESI, Pos. 20 V): 869 (2M+H)⁺, 435 (M+H)⁺, 290;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09484-azepan-1-yl-N-1-[4-(methylsulfonyl)benzyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 831 (2M+H)⁺, 416 (M+H)⁺, 193;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-09494-azepan-1-yl-N-(1-[5-(2-chlorophenyl)-2-furyl]methylazetidin-3-yl)pyrimidin-2-amine

MS (ESI, Pos. 20 V): 440, 438 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-09504-azepan-1-yl-N-1-[(3-phenyl-1H-pyrazol-4-yl)methyl]azetidin-3-ylpyrimidin-2-amine

MS (ESI, Pos. 20 V): 807 (2M+H)⁺, 404 (M+H)⁺, 248, 202.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-09514-azepan-1-yl-N-[1-(5-[2-(trifluoromethyl)phenyl]-2-furylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 472 (M+H)⁺, 225;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-09524-azepan-1-yl-N-[1-(5-[3-(trifluoromethyl)phenyl]-2-furylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 943 (2M+H)⁺, 472 (M+H)⁺, 225;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-09534-azepan-1-yl-N-[1-(5-[2-chloro-5-(trifluoromethyl)phenyl]-2-furylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 508, 506 (M+H)⁺, 248;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 11-09544-azepan-1-yl-N-[1-(5-[2-(trifluoromethoxy)phenyl]-2-furylmethyl)azetidin-3-yl]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 975 (2M+H)⁺, 488 (M+H)⁺, 241;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 11-09554-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-methyloxime

MS (ESI, Pos. 20 V): 401 (M+H)⁺, 276, 177;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-09564-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-ethyloxime

MS (ESI, Pos. 20 V): 415 (M+H)⁺, 276, 208 (M+2H)²⁺, 177;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09574-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-allyloxime

MS (ESI, Pos. 20 V): 427 (M+H)⁺, 276, 214 (M+2H)²⁺, 177;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-09584-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-(tert-butyl)oxime

MS (ESI, Pos. 20 V): 443 (M+H)⁺, 276, 194, 112; HPLC condition: A; HPLCretention time (min): 3.20.

Example 11-09594-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-tetrahydro-2H-pyran-2-yloxime

MS (ESI, Pos. 20 V): 471 (M+H)⁺, 387, 276, 194;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-0960[(4-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexylidene)amino]oxyaceticacid

MS (ESI, Pos. 20 V): 445 (M+H)⁺, 416, 304, 185, 171;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-09614-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-isobutyloxime

MS (ESI, Pos. 20 V): 443 (M+H)⁺, 276, 222 (M+2H)²⁺, 177;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 11-09624-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-[2-(trimethylsilyl)ethyl]oxime

MS (ESI, Pos. 20 V): 487 (M+H)⁺, 387, 276, 230;

HPLC condition: A; HPLC retention time (min): 3.40.

Example 11-09634-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-phenyloxime

MS (ESI, Pos. 20 V): 925 (2M+H)⁺, 463 (M+H)⁺, 193, 177;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 11-09644-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-benzyloxime

MS (ESI, Pos. 20 V): 477 (M+H)⁺, 387, 239 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-09654-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]piperidin-1-ylcyclohexanoneO-trityloxime

MS (ESI, Pos. 20 V): 629 (M+H)⁺, 387, 243;

HPLC condition: A; HPLC retention time (min): 3.60.

Example 11-09663-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-phenyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 478 (M+H)⁺, 239.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-09673-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-butyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 458 (M+H)⁺, 276, 180;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 11-09683-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(4-chlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 514, 512 (M+H)⁺, 256.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-09693-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3-methylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 492 (M+H)⁺, 246.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09703-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3-chlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 514, 512 (M+H)⁺, 256.5 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-09713-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-cyclohexyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 484 (M+H)⁺, 276, 180;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-09723-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-chlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 514, 512 (M+H)⁺, 256.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-09733-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(4-methylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 492 (M+H)⁺, 246.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09743-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-ethyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 430 (M+H)⁺, 276, 180;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 11-09753-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3,4-dichlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 548, 546 (M+H)⁺, 466, 273.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-09763-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-[3-(trifluoromethyl)phenyl]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 546 (M+H)⁺, 466, 273.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 11-09773-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-methoxyphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 508 (M+H)⁺, 254.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-09783-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-hexyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 486 (M+H)⁺, 276, 180;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-09793-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3-methoxyphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 508 (M+H)⁺, 254.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09803-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(4-ethoxyphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 522 (M+H)⁺, 261.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09813-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(4-methoxyphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 508 (M+H)⁺, 254.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09823-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(1-naphthyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 528 (M+H)⁺, 264.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-09833-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-ethoxyphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 522 (M+H)⁺, 261.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-09843-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-[2-(trifluoromethyl)phenyl]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 546 (M+H)⁺, 253.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09853-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,4-dichlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 548, 546 (M+H)⁺, 465, 273.5 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.17.

Example 11-0986 ethylN-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylcarbonyl)glycinate

MS (ESI, Pos.20V): 488 (M+H)⁺, 221, 193;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-09873-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-methylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 492 (M+H)⁺, 246.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09883-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-fluorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 496 (M+H)⁺, 248.5 (M+2H)²⁺, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-09893-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3-fluorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 991 (2M+H)⁺, 496 (M+H)⁺, 248.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-09903-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,4-difluorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 514 (M+H)⁺, 257.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-09913-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(4-isopropylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 520 (M+H)⁺, 260.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-09923-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-ethylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 253.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09933-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-benzyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 492 (M+H)⁺, 372, 180;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 11-09943-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(4-fluorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 496 (M+H)⁺, 248.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-09953-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-[4-(trifluoromethyl)phenyl]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 546 (M+H)⁺, 466, 273.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-09963-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,5-dimethylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 253.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-09973-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-[3-(methylsulfanyl)phenyl]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 524 (M+H)⁺, 262.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-0998N-(1-adamantyl)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 536 (M+H)⁺, 461, 180;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-09993-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,4-dimethoxyphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 538 (M+H)⁺, 269.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-10003-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3,5-dimethylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 446, 253.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-1001N-(3-acetylphenyl)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 520 (M+H)⁺, 372, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-10023-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3,5-dichlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 548, 546 (M+H)⁺, 466, 273.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-10033-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,5-dichlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 548, 546 (M+H)⁺, 466, 273.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.15.

Example 11-10043-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-pentyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 472 (M+H)⁺, 276, 180;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-10053-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(1,1′-biphenyl-2-yl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 554 (M+H)⁺, 496, 277.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-10063-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,6-dichlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 548, 546 (M+H)⁺, 273.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-10073-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-phenylethyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-10083-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,4-dimethylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 253.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-10093-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,3-dichlorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 548, 546 (M+H)⁺, 273.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-1010N-(4-acetylphenyl)-3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 520 (M+H)⁺, 372, 193;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 11-10113-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3-cyanophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 503 (M+H)⁺, 252 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 11-1012 ethyl4-[(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylcarbonyl)amino]benzoate

MS (ESI, Pos.20V): 550 (M+H)⁺, 472, 275 5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-10133-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-[4-(methylsulfanyl)phenyl]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 524 (M+H)⁺, 262.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 11-10143-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,3-dimethylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 253.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-10153-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(4-phenoxyphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 570 (M+H)⁺, 478, 285.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 11-10163-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(3-ethylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 253.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 11-1017 ethylN-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylcarbonyl)methioninate

MS (ESI, Pos.20V): 562 (M+H)⁺, 281.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-1018 ethylN-(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylcarbonyl)phenylalaninate

MS (ESI, Pos.20V): 578 (M+H)⁺, 496, 289.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-1019 ethyl3-[(3-[(4-azepan-1-ylpyrimidin-2-yl)amino]-1,4′-bipiperidin-1′-ylcarbonyl)amino]benzoate

MS (ESI, Pos.20V): 550 (M+H)⁺, 275.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-10203-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2-isopropylphenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 520 (M+H)⁺, 260.5 (M+2H)²⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-10213-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-[(1R)-1-phenylethyl]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 506 (M+H)⁺, 180;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 11-10223-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-[(1R,25)-2-phenylcyclopropyl]-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 518 (M+H)⁺, 259.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 11-10233-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-isopropyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 444 (M+H)⁺, 276, 180;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 11-10243-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-(2,6-difluorophenyl)-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 514 (M+H)⁺, 372, 193;

HPLC condition: A;

HPLC retention time (min): 3.01.

Example 11-10253-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N,N-dimethyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 430 (M+H)⁺, 372, 193;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-1026N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(morpholin-4-ylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 472 (M+H)⁺, 372, 114;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 11-10273-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N,N-diethyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 458 (M+H)⁺, 372, 193;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 11-10283-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N,N-diisopropyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 486 (M+H)⁺, 359, 128;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 11-10293-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N-methyl-N-phenyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 492 (M+H)⁺, 359, 134;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 11-1030N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(10H-phenothiazin-10-ylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 584 (M+H)⁺, 359, 292.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 11-1031N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(9H-carbazol-9-ylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 552 (M+H)⁺, 468, 276.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 11-10323-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N,N-diphenyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 554 (M+H)⁺, 470, 359, 196;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 11-1033N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(pyrrolidin-1-ylcarbonyl)-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 456 (M+H)⁺, 372, 359;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 11-1034N-(4-azepan-1-ylpyrimidin-2-yl)-1′-[(4-methylpiperazin-1-yl)carbonyl]-1,4′-bipiperidin-3-amine

MS (ESI, Pos.20V): 485 (M+H)⁺, 227;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 11-10353-[(4-azepan-1-ylpyrimidin-2-yl)amino]-N,N-dibutyl-1,4′-bipiperidin-1′-carboxamide

MS (ESI, Pos.20V): 514 (M+H)⁺, 450, 359, 156;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 12-1 to Example 12-6

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionwere given.

Example 12-1N¹-[2-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-4-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (CD₃OD): δ 2.72 (s, 6H), 2.90 (t, J=6.00 Hz, 2H), 3.13 (t, J=6.30Hz, 2H), 3.74 (t, J=6.30 Hz, 2H), 3.94 (t, J=6.00 Hz, 2H), 4.81 (s, 2H),5.90 (d, J=6.00 Hz, 1H), 7.17 (m, 4H), 7.75 (d, J=6.00 Hz, 1H);

MS (ESI, Pos. 20 V): 298 (M+H)⁺, 224, 186;

HPLC condition: A; HPLC retention time (min): 2.85;

TLC: Rf 0.53 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 12-21-(4-[2-(dimethylamino)ethyl]aminopyrimidin-2-yl)piperidin-3-ol Example12-3N¹-[2-(2,3-dihydro-1H-indol-1-yl)pyrimidin-4-yl]-N²,N²-dimethylethane-1,2-diamine

MS (ESI, Pos, 20 V): 284 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.53.

Example 12-4N¹-[2-azepan-1-yl-5-(trifluoromethyl)pyrimidin-4-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.47 (m, 4H), 1.76 (m, 4H), 2.15 (s, 6H), 2.37 (t,J=7.00 Hz, 2H), 3.31 (m, 2H), 3.59 (m, 4H), 7.17 (m, 1H), 8.12 (s, 1H);

MS (ESI, Pos, 20 V): 332 (M+H)⁺;

TLC: Rf 0.49 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 12-5N¹-[2-azepan-1-yl-5-(4-methylphenyl)pyrimidin-4-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.48 (m, 4H), 1.70 (m, 4H), 2.13 (s, 6H), 2.32 (s, 3H),2.38 (t, J=6.80 Hz, 2H), 3.38 (dt, J=5.4, 6.8 Hz, 2H), 3.69 (t, J=6.3Hz, 4H), 6.02 (t, J=5.40 Hz, 1H), 7.20 (m, 4H), 7.61 (s, 1H);

MS (ESI, Pos, 20 V): 354 (M+H)⁺, 177.5 (M+2H)²⁺;

TLC: Rf 0.51 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 12-6N¹-[2-azepan-1-yl-5-(4-methoxyphenyl)pyrimidin-4-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.48 (m, 4H), 1.71 (m, 4H), 2.13 (s, 6H), 2.38 (t,J=6.80 Hz, 2H), 3.37 (dt, J=5.3, 6.8 Hz, 2H), 3.68 (t, J=6.0 Hz, 4H),3.76 (s, 3H), 5.98 (t, J=5.30 Hz, 1H), 6.98 (d, J=8.80 Hz, 2H), 7.23 (d,J=8.80 Hz, 2H), 7.59 (s, 1H);

MS (ESI, Pos, 20 V): 370 (M+H)⁺, 185.5 (M+2H)²⁺;

TLC: Rf 0.61 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-001 to Example 13-121

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 13-0014-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[(1S*,2S*)-2-morpholin-4-ylcyclohexyl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.24 (m, 4H), 1.72 (m, 3H), 2.32 (m, 3H), 2.62 (m, 2H),3.05 (m, 2H), 3.22 (m, 2H), 3.32 (m, 3H), 3.84 (m, 3H), 4.75 (s, 2H),6.28 (d, J=6.60 Hz, 1H), 7.06 (m, 1H), 7.19 (m, 4H), 7.31 (d, J=8.50 Hz,1H), 7.50 (m, 1H), 7.81 (d, J=7.40 Hz, 1H);

MS (ESI, Pos. 20 V): 887 (2M+H)⁺, 444 (M+H)⁺, 222.5 (M+2H)²⁺;

TLC: Rf 0.34 (AcOEt:MeOH=10:1).

Example 13-0024-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[(1S*,2S*)-2-(4-methylpiperazin-1-yl)cyclohexyl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.19 (m, 4H), 1.71 (m, 3H), 1.97 (s, 3H), 2.17 (m, 4H),2.37 (m, 3H), 2.61 (m, 2H), 3.06 (t, J=5.20 Hz, 2H), 3.37 (m, 1H), 3.81(m, 3H), 4.75 (s, 2H), 6.19 (d, J=6.60 Hz, 1H), 7.08 (m, 1H), 7.18 (m,4H), 7.32 (d, J=8.00 Hz, 1H), 7.50 (m, 1H), 7.80 (d, J=8.00 Hz, 1H);

MS (ESI, Pos. 20 V): 913 (2M+H)⁺, 457 (M+H)⁺, 229 (M+2H)²⁺;

TLC: Rf 0.57 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-0034-azepan-1-yl-N-[(3R)-1-benzylpyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 1.64 (m, 5H), 1.92 (m, 4H), 2.35 (m, 1H), 2.52 (m, 2H),2.72 (m, 1H), 2.91 (dd, J=9.40, 6.90 Hz, 1H), 3.63 (s, 2H), 3.86 (t,J=5.90 Hz, 4H), 4.62 (m, 1H), 5.31 (m, 1H), 6.99 (m, 1H), 7.28 (m, 5H),7.45 (m, 2H), 7.80 (d, J=8.20 Hz, 1H);

MS (ESI, Pos. 20 V): 402 (M+H)⁺, 312;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-0044-azepan-1-yl-N-[(3S)-1-benzylpyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 1.64 (m, 5H), 1.92 (m, 4H), 2.35 (m, 1H), 2.52 (m, 2H),2.72 (m, 1H), 2.91 (dd, J=9.50, 7.00 Hz, 1H), 3.63 (s, 2H), 3.86 (t,J=5.90 Hz, 4H), 4.62 (m, 1H), 5.35 (m, 1H), 7.00 (m, 1H), 7.28 (m, 5H),7.45 (m, 2H), 7.80 (d, J=8.10 Hz, 1H);

MS (ESI, Pos. 20 V): 402 (M+H)⁺, 312;

TLC: Rf 0.55 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-0054-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.54 (m, 4H), 1.74 (m, 6H), 2.18 (m, 1H), 2.59 (m, 1H),2.71 (m, 1H), 2.93 (m, 1H), 3.73 (s, 2H), 3.84 (m, 4H), 4.40 (m, 1H),6.70 (m, 1H), 6.98 (t, J=7.70 Hz, 1H) 7.25 (m, 2H), 7.46 (m, 2H), 7.74(t, J=7.50 Hz, 1H), 7.83 (d, J=8.80 Hz, 1H), 8.47 (d, J=4.40 Hz, 1H);

MS (ESI, Pos, 20 V): 403 (M+H)⁺, 202 (M+2H)⁺;

TLC: Rf 0.33 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-0064-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)pyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 0.86 (t, J=7.00 Hz, 6H), 1.33 (m, 6H), 1.66 (m, 4H), 1.81(m, 1H), 1.97 (m, 4H), 2.31 (m, 4H), 2.61 (m, 2H), 3.02 (m, 1H), 3.93(t, J=5.50 Hz, 4H), 4.53 (m, 1H), 7.06 (m, 1H), 7.52 (m, 2H), 7.80 (d,J=8.40 Hz, 1H);

MS (ESI, Pos. 20 V): 396 (M+H)⁺, 312;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0074-azepan-1-yl-N-[(3R)-1-isobutylpyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 0.91 (d, J=6.60 Hz, 6H), 1.66 (m, 6H), 1.94 (m, 4H), 2.22(dd, J=7.50, 3.10 Hz, 2H), 2.31 (m, 1H), 2.47 (m, 2H), 2.69 (m, 1H),2.84 (dd, J=9.50, 7.00 Hz, 1H) 3.87 (t, J=5.90 Hz, 4H), 4.60 (m, 1H),5.39 (m, 1H), 6.99 (m, 1H), 7.44 (m, 2H), 7.81 (d, J=8.80 Hz, 1H);

MS (ESI, Pos. 20 V): 368 (M+H)⁺;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0084-azepan-1-yl-N-[(3R)-1-(cyclohexylmethyl)pyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 0.88 (m, 2H), 1.18 (m, 2H), 1.26 (m, 2H), 1.45 (m, 1H),1.67 (m, 6H), 1.78 (m, 4H), 1.96 (m, 4H), 2.28 (m, 3H), 2.41 (m, 1H),2.61 (m, 2H), 2.99 (m, 1H), 3.92 (t, J=5.90 Hz, 4H), 4.56 (m, 1H), 7.05(m, 1H), 7.49 (m, 2H), 7.80 (d, J=8.40 Hz, 1H);

MS (ESI, Pos. 20 V): 408 (M+H)⁺, 204.5 (M+2H);

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0094-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 1.64 (m, 4H), 1.75 (m, 1H), 1.93 (m, 4H), 2.38 (m, 1H),2.60 (m, 2H), 2.82 (m, 1H), 2.97 (dd, J=9.90, 7.00 Hz, 1H), 3.76 (d,J=13.60 Hz, 1H), 3.83 (d, J=13.60 Hz, 1H), 3.87 (t, J=5.90 Hz, 4H), 4.65(m, 1H), 5.59 (m, 1H), 7.00 (m, 1H), 7.15 (dd, J=5.10, 1.10 Hz, 1H),7.45 (m, 3H), 7.65 (td, J=7.60, 1.80 Hz, 1H), 7.80 (d, J=8.40 Hz, 1H),8.55 (ddd, J=5.10, 1.80, 0.70 Hz, 1H);

MS (ESI, Pos. 20 V): 403 (M+H)⁺, 202 (M+2H)⁺;

TLC: Rf 0.35 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0104-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)pyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 0.86 (t, J=6.20 Hz, 6H), 1.36 (m, 6H), 1.66 (m, 5H), 1.95(m, 4H), 2.29 (m, 2H), 2.45 (m, 2H), 2.67 (m, 1H), 2.84 (m, 1H), 3.89(t, J=5.50 Hz, 4H), 4.59 (m, 1H), 5.68 (m, 1H), 7.01 (m, 1H), 7.46 (m,2H), 7.81 (d, J=8.40 Hz, 1H);

MS (ESI, Pos. 20 V): 396 (M+H)⁺, 312, 243;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0114-azepan-1-yl-N-[(3S)-1-isobutylpyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 0.92 (d, J=6.60 Hz, 6H), 1.66 (m, 6H), 1.95 (m, 4H), 2.23(dd, J=7.70, 2.90 Hz, 2H), 2.31 (m, 1H), 2.48 (m, 2H), 2.67 (m, 1H),2.89 (m, 1H), 3.90 (t, J=5.50 Hz, 4H), 4.59 (m, 1H), 5.93 (m, 1H), 7.03(m, 1H), 7.47 (m, 2H), 7.81 (d, J=8.10 Hz, 1H);

MS (ESI, Pos. 20 V): 368 (M+H)⁺, 184.5 (M+2H)⁺;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0124-azepan-1-yl-N-[(3S)-1-(cyclohexylmethyl)pyrrolidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 0.89 (m, 2H), 1.20 (m, 4H), 1.45 (m, 1H), 1.67 (m, 6H),1.78 (m, 3H), 1.96 (m, 4H), 2.29 (dd, J=7.30, 2.90 Hz, 2H), 2.36 (m,1H), 2.40 (m, 1H), 2.62 (m, 2H), 2.99 (m, 1H), 3.92 (t, J=5.90 Hz, 4H),4.57 (m, 1H), 7.07 (m, 1H), 7.50 (m, 2H), 7.81 (d, J=8.10 Hz, 1H);

MS (ESI, Pos. 20 V): 408 (M+H)⁺, 312, 243;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0134-azepan-1-yl-N-[(3S)-1-cyclohexylpyrrolidin-3-yl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.16 (m, 6H), 1.56 (m, 4H), 1.65 (m, 3H), 1.85 (m, 7H),2.05 (m, 2H), 2.39 (m, 1H), 2.59 (m, 1H), 2.91 (t, J=8.40 Hz, 1H), 3.81(t, J=5.30 Hz, 4H), 4.33 (m, 1H), 6.62 (m, 1H), 6.97 (t, J=8.10 Hz, 1H),7.25 (d, J=8.10 Hz, 1H), 7.44 (t, J=8.10 Hz, 1H), 7.82 (d, J=8.10 Hz,1H);

MS (ESI, Pos. 20 V): 394 (M+H)⁺, 312, 197.5 (M+2H)²⁺;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-0144-azepan-1-yl-N-[(3R)-1-cyclohexylpyrrolidin-3-yl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.16 (m, 6H), 1.56 (m, 4H), 1.66 (m, 3H), 1.86 (m, 7H),2.05 (m, 2H), 2.39 (m, 1H), 2.59 (m, 1H), 2.90 (t, J=8.10 Hz, 1H), 3.81(t, J=5.50 Hz, 4H), 4.33 (m, 1H), 6.57 (m, 1H), 6.97 (t, J=8.20 Hz, 1H),7.25 (d, J=8.20 Hz, 1H), 7.44 (t, J=8.20 Hz, 1H), 7.82 (d, J=8.20 Hz,1H);

MS (ESI, Pos. 20 V): 394 (M+H)⁺, 312, 197.5 (M+2H)²⁺;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 13-015N¹,N¹-dimethyl-N²-(4-piperidin-1-ylquinazolin-2-yl)ethane-1,2-diamine

MS (ESI, Pos.20V): 300 (M+H)⁺, 157;

HPLC condition: A; HPLC retention time (min): 3.04.

Example 13-0164-piperidin-1-yl-N-(2-pyrrolidin-1-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 326 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.94.

Example 13-0174-piperidin-1-yl-N-(2-piperidin-1-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 340 (M+H)⁺, 170.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 13-018 N-benzyl-4-piperidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 637 (2M+H)⁺, 319 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.55.

Example 13-019 N-(2-phenyl ethyl)-4-piperidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 333 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.64.

Example 13-020 N-isopentyl-4-piperidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 597 (2M+H)⁺, 299 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.67.

Example 13-021 4-piperidin-1-yl-N-(thien-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 325 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.62.

Example 13-022 N-(2-furylmethyl)-4-piperidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 309 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 13-023 4-piperidin-1-yl-N-(pyridin-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 320 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.90.

Example 13-0244-piperidin-1-yl-N-(2-pyridin-2-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 334 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 13-025N-[(5-methylpyrazin-2-yl)methyl]-4-piperidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 669 (2M+H)⁺, 335 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 13-026 4-azepan-1-yl-N-(2-piperidin-1-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 354 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 13-027N¹-(4-azepan-1-ylquinazolin-2-yl)-N³,N³-dimethylpropane-1,3-diamine

MS (ESI, Pos.20V): 328 (M+H)⁺, 157;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 13-028 4-azepan-1-yl-N-benzylquinazolin-2-amine

MS (ESI, Pos.20V): 665 (2M+H)⁺, 333 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.64.

Example 13-029 4-azepan-1-yl-N-(2-phenylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 693 (2M+H)⁺, 347 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.71.

Example 13-030 4-azepan-1-yl-N-isopentylquinazolin-2-amine

MS (ESI, Pos.20V): 313 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.73.

Example 13-031 4-azepan-1-yl-N-(thien-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 339 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.58.

Example 13-032 4-azepan-1-yl-N-(2-furylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 323 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.49.

Example 13-033 4-azepan-1-yl-N-(pyridin-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 334 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.96.

Example 13-034 4-azepan-1-yl-N-(2-pyridin-2-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 348 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.00.

Example 13-0354-azepan-1-yl-N-[(5-methylpyrazin-2-yl)methyl]quinazolin-2-amine

MS (ESI, Pos.20V): 349 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 13-036 N-benzyl-4-pyrrolidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 609 (2M+H)⁺, 305 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.43.

Example 13-037 N-(2-phenylethyl)-4-pyrrolidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 319 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.55.

Example 13-038 N-isopentyl-4-pyrrolidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 569 (2M+H)⁺, 285 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.58.

Example 13-039 4-pyrrolidin-1-yl-N-(thien-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 621 (2M+H)⁺, 311 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 13-040 N-(2-furylmethyl)-4-pyrrolidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 589 (2M+H)⁺, 295 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.36.

Example 13-041N-(pyridin-2-ylmethyl)-4-pyrrolidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 306 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 13-042N-(2-pyridin-2-ylethyl)-4-pyrrolidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 320 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 13-043N-[(5-methylpyrazin-2-yl)methyl]-4-pyrrolidin-1-ylquinazolin-2-amine

MS (ESI, Pos.20V): 321 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.04.

Example 13-044 4-azocan-1-yl-N-benzylquinazolin-2-amine

MS (ESI, Pos.20V): 693 (2M+H)⁺, 347 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.71.

Example 13-045 4-azocan-1-yl-N-(2-phenylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 721 (2M+H)⁺, 361 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.78.

Example 13-046 4-azocan-1-yl-N-isopentylquinazolin-2-amine

MS (ESI, Pos.20V): 653 (2M+H)⁺, 327 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.86.

Example 13-047 4-azocan-1-yl-N-(thien-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 353 (M+H)⁺, 257

HPLC condition: A; HPLC retention time (min): 3.69.

Example 13-048 4-azocan-1-yl-N-(2-furylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 337 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.60.

Example 13-049 4-azocan-1-yl-N-(pyridin-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 348 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.02.

Example 13-050 4-azocan-1-yl-N-(2-pyridin-2-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 723 (2M+H)⁺, 362 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 13-0514-azocan-1-yl-N-[(5-methylpyrazin-2-yl)methyl]quinazolin-2-amine

MS (ESI, Pos.20V): 725 (2M+H)⁺, 363 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 13-0524-(3-azabicyclo[3.2.2]non-3-yl)-N-benzylquinazolin-2-amine

MS (ESI, Pos.20V): 717 (2M+H)⁺, 359 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.75.

Example 13-0534-(3-azabicyclo[3.2.2]non-3-yl)-N-(2-phenylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 745 (2M+H)⁺, 373 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.84.

Example 13-0544-(3-azabicyclo[3.2.2]non-3-yl)-N-isopentylquinazolin-2-amine

MS (ESI, Pos.20V): 339 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.88.

Example 13-0554-(3-azabicyclo[3.2.2]non-3-yl)-N-(pyridin-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 360 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.01.

Example 13-0564-(3-azabicyclo[3.2.2]non-3-yl)-N-(2-pyridin-2-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 374 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 13-0574-(3-azabicyclo[3.2.2]non-3-yl)-N-[(5-methylpyrazin-2-yl)methyl]quinazolin-2-amine

MS (ESI, Pos.20V): 749 (2M+H)⁺, 375 (M+H)⁺; HPLC condition: A; HPLCretention time (min): 3.31.

Example 13-0582,2′-[(2-[4-(3,4-dihydro-2(1H)-isoquinolinyl)-2-quinazolinyl]aminoethyl)imino]diethanol

MS (ESI, Pos.20V): 815 (2M+H)⁺, 408 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 13-0594-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[3-(1H-imidazol-1-yl)propyl]quinazolin-2-amine

MS (ESI, Pos.20V): 769 (2M+H)⁺, 385 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.06.

Example 13-0604-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(2-morpholin-4-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 779 (2M+H)⁺, 390 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.02.

Example 13-0614-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-pyrrolidin-1-ylpropyl)quinazolin-2-amine

MS (ESI, Pos.20V): 388 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 13-0624-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]quinazolin-2-amine

MS (ESI, Pos.20V): 388 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-0634-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[(1-ethylpyrrolidin-2-yl)methyl]quinazolin-2-amine

MS (ESI, Pos.20V): 775 (2M+H)⁺, 388 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 13-064N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-yl]-N³,N³,2,2-tetramethylpropane-1,3-diamine

MS (ESI, Pos.20V): 779 (2M+H)⁺, 390 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 13-065N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-yl]-N²,N²-dimethylpropane-1,2-diamine

MS (ESI, Pos.20V): 362 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-066N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-yl]-N²,N²-diethylethane-1,2-diamine

MS (ESI, Pos.20V): 376 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-067N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-yl]-N³,N³-diethylpropane-1,3-diamine

MS (ESI, Pos.20V): 390 (M+H)⁺, 195.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 13-0684-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-morpholin-4-ylpropyl)quinazolin-2-amine

MS (ESI, Pos.20V): 404 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-0692,2′-[(3-[4-(3,4-dihydro-2(1H)-isoquinolinyl)-2-quinazolinyl]aminopropyl)imino]diethanol

MS (ESI, Pos.20V): 422 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 13-070N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-yl]-N³,N³-dimethylpropane-1,3-diamine

MS (ESI, Pos.20V): 362 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 13-071N²-[4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-yl]-N¹,N¹-dimethylpropane-1,2-diamine

MS (ESI, Pos.20V): 362 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 13-0724-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[3-(2-methylpiperidin-1-yl)propyl]quinazolin-2-amine

MS (ESI, Pos.20V): 416 (M+H)⁺, 208.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 13-0734-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[(1-methylpyrrolidin-2-yl)methyl]quinazolin-2-amine

MS (ESI, Pos.20V): 374 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-074N-benzyl-4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-amine

MS (ESI, Pos.20V): 733 (2M+H)⁺, 367 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.62.

Example 13-0754-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(2-phenylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 761 (2M+H)⁺, 381 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.69.

Example 13-0764-(3,4-dihydroisoquinolin-2(1H)-yl)-N-isopentylquinazolin-2-amine

MS (ESI, Pos.20V): 693 (2M+H)⁺, 347 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.75.

Example 13-0774-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(thien-2-ylmethyl)quinazolin-2-amineExample 13-0784-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(2-furylmethyl)quinazolin-2-amineExample 13-0794-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(pyridin-2-ylmethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 368 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.03.

Example 13-0804-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(2-pyridin-2-ylethyl)quinazolin-2-amine

MS (ESI, Pos.20V): 382 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 13-0814-(3,4-dihydroisoquinolin-2(1H)-yl)-N-[(5-methylpyrazin-2-yl)methyl]quinazolin-2-amine

MS (ESI, Pos.20V): 765 (2M+H)⁺, 383 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 13-0824-azepan-1-yl-N-[(3S)-1-benzylazepan-3-yl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.57 (m, 9H), 1.86 (m, 5H), 2.59 (m, 3H), 2.84 (dd,J=13.20, 4.00 Hz, 1H), 3.65 (s, 2H), 3.79 (m, 4H), 4.08 (m, 1H), 6.20(m, 1H), 6.96 (m, 1H), 7.26 (m, 6H), 7.42 (m, 1H), 7.79 (d, J=8.40 Hz,1H);

MS (ESI, Pos. 20 V): 430 (M+H)⁺, 290, 193;

HPLC condition: A; HPLC retention time (min): 3.20;

TLC: Rf 0.40 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-0834-azepan-1-yl-N-[(3R)-1-benzylazepan-3-yl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.48 (m, 8H), 1.82 (m, 4H), 2.61 (m, 3H), 2.84 (dd,J=13.00, 3.80 Hz, 1H), 3.16 (d, J=5.30 Hz, 2H), 3.65 (s, 2H), 3.78 (m,4H), 4.06 (m, 1H), 6.19 (m, 1H), 6.95 (t, J=7.70 Hz, 1H), 7.23 (m, 6H),7.42 (m, 1H), 7.79 (d, J=8.20 Hz, 1H);

MS (ESI, Pos. 20 V): 430 (M+H)⁺, 340;

HPLC condition: A; HPLC retention time (min): 3.18;

TLC: Rf 0.40 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-084 N-[(3S)-azepan-3-yl]-4-azepan-1-ylquinazolin-2-amine

NMR (DMSO-d₆): δ 1.51 (m, 10H), 1.84 (m, 5H), 2.63 (dd, J=13.50, 7.20Hz, 1H), 2.74 (t, J=5.80 Hz, 1H), 2.94 (dd, J=13.50, 4.10 Hz, 1H), 3.80(m, 4H), 4.04 (m, 1H), 6.21 (m, 1H), 6.95 (t, J=7.60 Hz, 1H), 7.23 (d,J=8.20 Hz, 1H), 7.43 (t, J=7.60 Hz, 1H), 7.80 (d, J=8.20 Hz, 1H);

MS (ESI, Pos. 20 V): 340 (M+H)⁺, 170.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07;

TLC: Rf 0.22 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-085 N-[(3R)-azepan-3-yl]-4-azepan-1-ylquinazolin-2-amine

NMR (DMSO-d₆): δ 1.57 (m, 10H), 1.84 (m, 5H), 2.63 (dd, J=13.60, 7.10Hz, 1H), 2.74 (t, J=6.00 Hz, 1H), 2.93 (dd, J=13.60, 4.40 Hz, 1H), 3.80(m, 4H), 4.04 (m, 1H), 6.23 (m, 1H), 6.95 (t, J=7.10 Hz, 1H), 7.23 (d,J=8.10 Hz, 1H), 7.43 (m, 1H), 7.80 (d, J=8.10 Hz, 1H);

MS (ESI, Pos. 20 V): 340 (M+H)⁺, 170.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07;

TLC: Rf 0.24 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-0864-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)azepan-3-yl]quinazolin-2-amineExample 13-0874-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)azepan-3-yl]quinazolin-2-amineExample 13-0884-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)azepan-3-yl]quinazolin-2-amine

MS (ESI, Pos. 20 V): 424 (M+H)⁺, 340, 212.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.31.

Example 13-0894-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)azepan-3-yl]quinazolin-2-amine

MS (ESI, Pos. 20 V): 424 (M+H)⁺, 340, 212.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 13-0904-azepan-1-yl-N-[(3S)-1-isobutylazepan-3-yl]quinazolin-2-amine

MS (ESI, Pos. 20 V): 396 (M+H)⁺, 340, 198.5 (M+2H)²⁺; HPLC condition: A;HPLC retention time (min): 3.16.

Example 13-0914-azepan-1-yl-N-[(3R)-1-isobutylazepan-3-yl]quinazolin-2-amine

MS (ESI, Pos. 20 V): 396 (M+H)⁺, 340, 198.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 13-0924-azepan-1-yl-N-[(3S)-1-cyclohexylazepan-3-yl]quinazolin-2-amine

MS (ESI, Pos. 20 V): 422 (M+H)⁺, 396, 340, 211.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 13-0934-azepan-1-yl-N-[(3R)-1-cyclohexylazepan-3-yl]quinazolin-2-amine

MS (ESI, Pos. 20 V): 422 (M+H)⁺, 396, 340, 211.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 13-0944-azepan-1-yl-N-[(3S)-1-benzylpiperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 831 (2M+H)⁺, 416 (M+H)⁺, 326;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 13-0954-azepan-1-yl-N-[(3S)-1-benzylpiperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 831 (2M+H)⁺, 416 (M+H)⁺, 326;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 13-0964-azepan-1-yl-N-[(3R)-1-benzylpiperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 417 (M+H)⁺, 209 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-0974-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)piperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 417 (M+H)⁺, 209 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-0984-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)piperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 819 (2M+H)⁺, 410 (M+H)⁺, 326, 205.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 13-0994-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)piperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 819 (2M+H)⁺, 410 (M+H)⁺, 326, 205.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 13-1004-azepan-1-yl-N-[(3S)-1-isobutylpiperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 763 (2M+H)⁺, 382 (M+H)⁺, 191.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 13-1014-azepan-1-yl-N-[(3R)-1-isobutylpiperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 764 (2M+H)⁺, 382 (M+H)⁺, 191.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 13-1024-azepan-1-yl-N-[(3S)-1-cyclohexylpiperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 815 (2M+H)⁺, 408 (M+H)⁺, 326, 204.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 13-1034-azepan-1-yl-N-[(3R)-1-cyclohexylpiperidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 815 (2M+H)⁺, 408 (M+H)⁺, 326, 204.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 13-104 4-azepan-1-yl-N-[(3S)-piperidin-3-yl]quinazolin-2-amine

NMR (CDCl₃): δ 1.54 (m, 2H), 1.65 (m, 4H), 1.78 (m, 1H), 1.95 (m, 5H),2.18 (m, 1H), 2.58 (dd, J=11.80, 8.20 Hz, 1H), 2.67 (m, 1H), 2.91 (m,1H), 3.28 (dd, J=11.80, 3.40 Hz, 1H), 3.87 (t, J=5.70 Hz, 4H), 4.00 (m,1H), 5.27 (m, 1H), 7.00 (m, 1H), 7.45 (m, 2H), 7.81 (m, 1H);

MS (ESI, Pos. 20 V): 326 (M+H)⁺, 163.5 (M+2H)²⁺;

TLC: Rf 0.17 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-105 4-azepan-1-yl-N-[(3R)-piperidin-3-yl]quinazolin-2-amine

NMR (DMSO-d₆): δ 1.41 (m, 2H), 1.59 (m, 5H), 1.85 (m, 5H), 2.37 (m, 2H),2.76 (m, 1H), 3.01 (dd, J=11.40, 3.50 Hz, 1H), 3.80 (m, 5H), 6.27 (m,1H), 6.96 (t, J=7.60 Hz, 1H), 7.24 (d, J=8.20 Hz, 1H), 7.43 (t, J=7.60Hz, 1H), 7.80 (d, J=8.20 Hz, 1H);

MS (ESI, Pos. 20 V): 326 (M+H)⁺, 163.5 (M+2H)²⁺;

TLC: Rf 0.17 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 13-106 4-azepan-1-yl-N-(1-benzylazetidin-3-yl)quinazolin-2-amine

MS (ESI, Pos.20V): 388 (M+H)⁺, 298;

HPLC condition: A; HPLC retention time (min): 3.18.

Example 13-1074-azepan-1-yl-N-[1-(pyridin-2-ylmethyl)azetidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 389 (M+H)⁺, 195 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-1084-azepan-1-yl-N-[1-(2-ethylbutyl)azetidin-3-yl]quinazolin-2-amine

MS (ESI, Pos.20V): 382 (M+H)⁺, 298, 191.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 13-1094-azepan-1-yl-N-(1-isobutylazetidin-3-yl)quinazolin-2-amine

MS (ESI, Pos.20V): 354 (M+H)⁺, 298, 177.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.09.

Example 13-1104-azepan-1-yl-N-(1-cyclohexylazetidin-3-yl)quinazolin-2-amine

MS (ESI, Pos.20V): 380 (M+H)⁺, 298, 190.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 13-111 4-azepan-1-yl-N-azetidin-3-ylquinazolin-2-amine

MS (ESI, Pos.20V): 298 (M+H)⁺, 149.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.89.

Example 13-112 2,4-dipiperidin-1-ylquinazoline

MS (ESI, Pos. 20 V): 297 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.42.

Example 13-113N¹-(4-azepan-1-ylquinazolin-2-yl)-N²,N²-dimethylethane-1,2-diamine

MS (ESI, Pos. 20 V): 314 (M+H)⁺, 157.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.92.

Example 13-114 2,4-diazepan-1-ylquinazoline

MS (ESI, Pos. 20 V): 325 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.62.

Example 13-115N¹-[4-(3,4-dihydroisoquinolin-2(1H)-yl)quinazolin-2-yl]-N²,N²-dimethylethane-1,2-diamine

MS (ESI, Pos. 20 V): 348 (M+H)⁺, 174.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.02.

Example 13-1164-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(2-pyrrolidin-1-ylethyl)quinazolin-2-amine

MS (ESI, Pos. 20 V): 374 (M+H)⁺, 187.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.07.

Example 13-1174-(3,4-dihydroisoquinolin-2(1H)-yl)-N-(2-piperidin-1-ylethyl)quinazolin-2-amine

MS (ESI, Pos. 20 V): 388 (M+H)⁺, 194.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.60.

Example 13-118 4-azepan-1-yl-N-isopentylquinazolin-2-amine

MS (ESI, Pos. 20 V): 625 (2M+H)⁺, 313 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.73.

Example 13-119N¹-(4-azepan-1-ylquinazolin-2-yl)-N¹,N²,N²-trimethylethane-1,2-diamine

NMR (CDCl₃): δ 7.83 (d, J=7.5 Hz, 1H), 7.44 (dd, J=7.5, 6.6 Hz, 1H),7.27 (d, J=8.7 Hz, 1H), 6.97 (dd, J=8.7, 6.6 Hz, 1H), 3.82 (m, 4H), 3.69(t, J=6.9 Hz, 2H), 3.11 (s, 3H), 2.41 (t, J=6.9 Hz, 2H), 2.17 (s, 6H),1.87 (m, 4H), 1.55 (m, 4H);

MS (ESI, Pos. 20 V): 328 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.98.

Example 13-120N²-(4-azepan-1-ylquinazolin-2-yl)-N¹,N¹-dimethylglycinamide

NMR (CDCl₃): δ 7.85 (d, J=7.2 Hz, 1H), 7.47 (dd, J=7.2, 7.2 Hz, 1H),7.25 (d, J=8.4 Hz, 1H), 7.00 (dd, J=8.4, 7.2 Hz, 1H), 4.10 (d, J=5.4 Hz,2H), 3.81 (m, 4H), 3.01 (s, 3H), 2.84 (s, 3H), 1.85 (m, 4H), 1.55 (m,4H);

MS (ESI, Pos. 20 V): 328 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.12.

Example 13-1214-azepan-1-yl-N-(1-methyl-2-piperidin-1-ylethyl)quinazolin-2-amineExample 14-01 to Example 14-84

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 14-01N¹-(6-azepan-1-ylpyrimidin-4-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 7.93 (s, 1H), 6.32 (m, 1H), 5.44 (s, 1H), 3.49 (m, 4H),3.25 (dt, J=6.0, 6.3 Hz, 2H), 2.34 (t, J=6.3 Hz, 2H), 2.15 (s, 6H), 1.65(m, 4H), 1.44 (m, 4H);

MS (ESI, Pos. 20 V): 264 (M+H)⁺, 219, 132.5 (M+2H)²⁺;

TLC: Rf 0.38 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-02N¹-(4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.47 (m, 4H), 1.67 (m, 4H), 1.85 (m, 2H), 2.18 (s, 6H),2.39 (t, J=6.90 Hz, 2H), 2.86 (m, 2H), 3.27 (m, 4H), 3.61 (t, J=6.00 Hz,4H), 5.95 (m, 1H);

MS (ESI, Pos. 20 V): 304 (M+H)⁺, 152.5 (M+2H)²⁺;

TLC: Rf 0.31 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-03N¹-(4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.49 (m, 4H), 1.58 (m, 2H), 1.70 (m, 6H), 2.18 (s, 6H),2.41 (m, 4H), 3.26 (m, 4H), 3.51 (m, 4H), 5.97 (m, 1H);

MS (ESI, Pos. 20 V): 318 (M+H)⁺, 159.5 (M+2H)²⁺;

TLC: Rf 0.31 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-04N¹-(4-azepan-1-yl-6-chloropyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (CDCl₃): δ 1.55 (m, 4H), 1.78 (m, 4H), 2.28 (s, 6H), 2.51 (t, J=6.30Hz, 2H), 3.46 (m, 6H), 5.33 (m, 1H), 5.79 (s, 1H);

MS (ESI, Pos. 20 V): 300, 298 (M+H)⁺;

TLC: Rf 0.45 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-05N¹-(4-azepan-1-yl-6-methoxyquinazolin-2-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (CDCl₃): 1.69 (m, 4H), 1.97 (m, 4H), 2.27 (s, 6H), 2.53 (t, J=6.50Hz, 2H), 3.56 (m, 2H), 3.85 (m, 4H), 3.82 (s, 3H), 5.40 (m, 1H), 7.21(m, 2H), 7.45 (d, J=9.60 Hz, 1H);

MS (ESI, Pos. 20 V): 344 (M+H)⁺, 172.5 (M+2H)²⁺;

TLC: Rf 0.43 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-06N¹-(4-azepan-1-yl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (CD₃OD): δ 1.63 (m, 8H), 1.82 (m, 6H), 2.32 (s, 6H), 2.59 (m, 4H),2.70 (m, 2H), 3.47 (t, J=6.80 Hz, 2H), 3.54 (m, 4H);

MS (ESI, Pos. 20 V): 332 (M+H)⁺, 318, 166.5 (M+2H)²⁺;

TLC: Rf 0.40 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-07N¹-[4-azepan-1-yl-5-(trifluoromethyl)pyrimidin-2-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.46 (m, 4H), 1.69 (m, 4H), 2.16 (s, 6H), 2.41 (t,J=6.50 Hz, 2H), 3.44 (q, J=6.50 Hz, 2H), 3.69 (m, 4H), 6.61 (m, 1H),8.04 (s, 1H);

MS (ESI, Pos. 20 V): 332 (M+H)⁺, 166.5 (M+2H)²⁺;

TLC: Rf 0.69 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-08N-(4-piperidin-1-ylthieno[3,2-d]pyrimidin-2-yl)ethane-1,2-diamine

NMR (CDCl₃): 1.68 (m, 6H), 2.01 (m, 2H), 2.94 (m, 2H), 3.50 (q, J=5.70Hz, 2H), 3.86 (t, J=5.70 Hz, 4H), 5.05 (m, 1H), 7.10 (d, J=5.10 Hz, 1H),7.53 (d, J=5.10 Hz, 1H);

MS (EI, Pos.): 277 (M+), 247, 235, 219, 205, 191, 179, 165, 151, 135;

TLC: Rf 0.15 (CH₂Cl₂:MeOH:NH₄OH=80:10:1).

Example 14-09N-(4-azepan-1-ylthieno[3,2-d]pyrimidin-2-yl)butane-1,4-diamine

NMR (CDCl₃): δ 1.60 (m, 8H), 1.86 (m, 6H), 2.74 (m, 2H), 3.42 (m, 2H),3.87 (t, J=6.00 Hz, 4H), 4.81 (m, 1H), 7.07 (d, J=5.50 Hz, 1H), 7.52 (d,J=5.50 Hz, 1H);

MS (EI, Pos.): 319 (M+), 303, 289, 276, 261, 248, 233, 219, 205;

TLC: Rf 0.13 (CH₂Cl₂:MeOH:NH₄OH=80:10:1).

Example 14-10N¹-[4-azepan-1-yl-5-(4-methylphenyl)pyrimidin-2-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.34 (m, 4H), 1.54 (m, 4H), 2.18 (s, 6H), 2.30 (s, 3H),2.41 (t, J=6.90 Hz, 2H), 3.31 (m, 6H), 6.33 (m, 1H), 7.15 (d, J=8.4 Hz,2H), 7.10 (d, J=8.4 Hz, 2H), 7.52 (s, 1H);

MS (ESI, Pos. 20 V): 354 (M+H)⁺, 177.5 (M+2H)²⁺;

TLC: Rf 0.31 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-11N¹-[4-azepan-1-yl-5-(4-methoxyphenyl)pyrimidin-2-yl]-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 1.36 (m, 4H), 1.52 (m, 4H), 2.18 (s, 6H), 2.41 (t,J=7.10 Hz, 2H), 3.31 (m, 6H), 3.75 (s, 3H), 6.30 (m, 1H), 6.91 (d,J=8.80 Hz, 2H), 7.14 (d, J=8.80 Hz, 2H), 7.51 (s, 1H);

MS (ESI, Pos. 20 V): 370 (M+H)⁺, 185.5 (M+2H)²⁺;

TLC: Rf 0.27 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-124-azepan-1-yl-N-[(3S)-1-benzylpyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.42 (m, 4H), 1.64 (m, 6H), 1.83 (m, 2H), 2.08 (m, 1H),2.25 (dd, J=9.20, 5.50 Hz, 2H), 2.42 (m, 2H), 2.76 (m, 1H), 2.85 (t,J=7.10 Hz, 2H), 3.52 (s, 2H), 3.57 (m, 4H), 4.23 (m, 1H), 6.21 (m, 1H),7.23 (m, 5H);

MS (ESI, Pos, 20 V): 392 (M+H)⁺, 302, 233;

TLC: Rf 0.44 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-134-azepan-1-yl-N-[(3R)-1-benzylpyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (CDCl₃): δ 1.53 (m, 4H), 1.71 (m, 5H), 1.96 (m, 2H), 2.29 (m, 1H),2.42 (m, 1H), 2.54 (m, 1H), 2.69 (m, 3H), 2.91 (m, 3H), 3.61 (s, 2H),3.66 (t, J=6.20 Hz, 4H), 4.44 (m, 1H), 5.27 (m, 1H), 7.32 (m, 5H);

MS (ESI, Pos. 20 V): 392 (M+H)⁺, 358, 302;

TLC: Rf 0.55 (AcOEt:MeOH:TEA=20:2:1).

Example 14-144-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.43 (m, 4H), 1.66 (m, 6H), 1.84 (m, 2H), 2.10 (m, 1H),2.33 (m, J=7.32, 7.32 Hz, 1H), 2.57 (m, 2H), 2.84 (m, 4H), 3.58 (t,J=6.00 Hz, 4H), 3.66 (s, 2H), 4.20 (m, 1H), 6.25 (m, 1H), 7.22 (m, 1H),7.41 (d, J=7.90 Hz, 1H), 7.72 (td, J=7.90, 1.70 Hz, 1H), 8.45 (m, 1H);

MS (ESI, Pos, 20 V): 393 (M+H)⁺, 197 (M+2H)²⁺;

TLC: Rf 0.41 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-154-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (CDCl₃): δ 1.54 (m, 4H), 1.73 (m, 5H), 2.01 (m, 2H), 2.31 (m, 1H),2.52 (dd, J=9.50, 5.50 Hz, 1H), 2.68 (m, 2H), 2.75 (t, J=8.00 Hz, 2H),2.93 (t, J=7.00 Hz, 2H), 3.03 (dd, J=9.50, 6.80 Hz, 1H), 3.69 (t, J=6.00Hz, 4H), 3.76 (d, J=13.70 Hz, 1H), 3.82 (d, J=13.70 Hz, 1H), 4.45 (m,1H), 6.94 (m, 1H), 7.15 (ddd, J=7.70, 4.90, 0.90 Hz, 1H), 7.43 (d,J=7.70 Hz, 1H), 7.65 (td, J=7.70, 1.70 Hz, 1H), 8.54 (ddd, J=4.90, 1.70,0.90 Hz, 1H);

MS (ESI, Pos. 20 V): 393 (M+H)⁺, 197 (M+2H)²⁺;

TLC: Rf 0.26 (AcOEt:MeOH:TEA=20:2:1).

Example 14-164-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)pyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.81 (m, 6H), 1.28 (m, 4H), 1.47 (m, 4H), 1.63 (m, 6H),1.85 (m, 2H), 2.05 (m, 1H), 2.22 (m, 2H), 2.48 (m, 5H), 2.75 (m, 1H),2.86 (m, 2H), 3.61 (t, J=6.00 Hz, 4H), 4.18 (m, 1H), 6.19 (m, 1H);

MS (ESI, Pos, 20 V): 386 (M+H)⁺, 233, 193.5 (M+2H)²⁺;

TLC: Rf 0.57 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-174-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)pyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (CDCl₃): δ 0.85 (t, J=7.10 Hz, 6H), 1.35 (m, 5H), 1.56 (m, 4H), 1.76(m, 5H), 1.99 (m, 2H), 2.31 (m, 4H), 2.61 (m, 2H), 2.72 (t, J=7.80 Hz,2H), 2.94 (m, 3H), 3.70 (t, J=6.00 Hz, 4H), 4.41 (m, 1H), 6.42 (m, 1H)

MS (ESI, Pos. 20 V): 386 (M+H)⁺, 302, 233, 193.5 (M+2H)²⁺;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 14-184-azepan-1-yl-N-[(3S)-1-isobutylpyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 0.84 (d, J=6.60 Hz, 6H), 1.45 (m, 4H), 1.61 (m, 6H),1.85 (m, 2H), 2.08 (m, 3H), 2.24 (m, 1H), 2.45 (m, 4H), 2.74 (m, 1H),2.86 (t, J=7.10 Hz, 2H), 3.61 (t, J=6.00 Hz, 4H), 4.19 (m, 1H), 6.17 (m,1H);

MS (ESI, Pos, 20 V): 358 (M+H)⁺, 233, 179.5 (M+2H)²⁺;

TLC: Rf 0.45 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-194-azepan-1-yl-N-[(3R)-1-isobutylpyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (CDCl₃): δ 0.91 (d, J=6.60 Hz, 6H), 1.55 (m, 4H), 1.75 (m, 6H), 1.97(m, 2H), 2.25 (m, 3H), 2.41 (m, 1H), 2.52 (m, 1H), 2.62 (m, 1H), 2.69(t, J=7.80 Hz, 2H), 2.87 (m, 1H), 2.94 (t, J=7.20 Hz, 2H), 3.68 (t,J=6.00 Hz, 4H), 4.44 (m, 1H), 5.26 (m, 1H);

MS (ESI, Pos. 20 V): 358 (M+H)⁺, 179.5 (M+2H)²⁺;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 14-204-azepan-1-yl-N-[(3S)-1-benzylpyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.41 (m, 4H), 1.65 (m, 8H), 2.10 (m, 1H), 2.24 (dd,J=9.00, 5.60 Hz, 1H), 2.45 (m, 6H), 2.78 (dd, J=9.00, 7.10 Hz, 1H), 3.34(m, 1H), 3.48 (t, J=6.00 Hz, 4H), 4.03 (s, 2H), 4.23 (m, 1H), 6.19 (m,1H), 7.23 (m, 5H);

MS (ESI, Pos, 20 V): 406 (M+H)⁺, 316;

TLC: Rf 0.43 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-214-azepan-1-yl-N-[(3R)-1-benzylpyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (CDCl₃): 1.54 (m, 4H), 1.66 (m, 4H), 1.75 (m, 5H), 2.27 (m, 1H),2.41 (dd, J=9.50, 4.80 Hz, 1H), 2.48 (m, 3H), 2.60 (m, 3H), 2.90 (dd,J=9.50, 6.60 Hz, 1H), 3.57 (t, J=6.20 Hz, 4H), 3.60 (s, 2H), 4.43 (m,1H), 5.12 (m, 1H), 7.26 (m, 5H);

MS (ESI, Pos. 20 V): 406 (M+H)⁺, 316;

TLC: Rf 0.55 (AcOEt:MeOH:TEA=20:2:1).

Example 14-224-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.45 (m, 4H), 1.59 (m, 10H), 2.09 (m, 1H), 2.32 (m,3H), 2.48 (m, 4H), 2.84 (t, J=7.80 Hz, 1H), 3.49 (t, J=5.80 Hz, 4H),3.66 (s, 2H), 4.20 (m, 1H), 6.23 (m, 1H), 7.23 (m, 1H), 7.41 (d, J=7.90Hz, 1H), 7.72 (m, 1H);

MS (ESI, Pos, 20 V): 407 (M+H)⁺, 204 (M+2H)²⁺;

TLC: Rf 0.36 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-234-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (CDCl₃): δ 1.55 (m, 4H), 1.66 (m, 3H), 1.76 (m, 6H), 2.30 (m, 1H),2.49 (m, 3H), 2.64 (m, 3H), 2.73 (m, 1H), 2.99 (dd, J=9.50, 6.80 Hz,1H), 3.62 (t, J=5.90 Hz, 4H), 3.75 (d, J=13.70 Hz, 1H), 3.81 (d, J=13.70Hz, 1H), 4.45 (m, 1H), 6.36 (m, 1H), 7.15 (ddd, J=7.60, 4.80, 1.20 Hz,1H), 7.43 (d, J=7.60 Hz, 1H), 7.65 (td, J=7.60, 1.80 Hz, 1H), 8.54 (ddd,J=4.80, 1.80, 1.20 Hz, 1H);

MS (ESI, Pos. 20 V): 407 (M+H)⁺, 204 (M+2H)²⁺;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 14-244-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)pyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 0.80 (m, 6H), 1.28 (m, 4H), 1.48 (m, 4H), 1.63 (m,10H), 2.03 (m, 1H), 2.22 (m, 3H), 2.49 (m, 6H), 2.79 (m, 1H), 3.51 (t,J=5.90 Hz, 4H), 4.17 (m, 1H), 6.15 (m, 1H);

MS (ESI, Pos, 20 V): 400 (M+H)⁺, 200.5 (M+2H)²⁺;

TLC: Rf 0.40 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-254-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)pyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (CDCl₃): δ 0.85 (t, J=6.40 Hz, 6H), 1.35 (m, 5H), 1.57 (m, 4H), 1.67(m, 4H), 1.78 (m, 5H), 2.27 (m, 3H), 2.35 (dd, J=9.50, 4.90 Hz, 1H),2.49 (t, J=5.90 Hz, 2H), 2.58 (m, 2H), 2.64 (t, J=6.60 Hz, 2H), 2.88(dd, J=9.20, 6.80 Hz, 1H), 3.63 (t, J=5.90 Hz, 4H), 4.40 (m, 1H), 5.97(m, 1H);

MS (ESI, Pos. 20 V): 400 (M+H)⁺, 316, 200.5 (M+2H)²⁺;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 14-264-azepan-1-yl-N-[(3S)-1-isobutylpyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 0.84 (d, J=6.60 Hz, 6H), 1.49 (m, 4H), 1.62 (m, 10H),2.07 (m, 3H), 2.23 (m, 1H), 2.47 (m, 6H), 2.75 (m, 1H), 3.51 (m, 4H),4.17 (m, 1H), 6.15 (m, 1H);

MS (ESI, Pos, 20 V): 372 (M+H)⁺, 186.5 (M+2H)²⁺;

TLC: Rf 0.38 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-274-azepan-1-yl-N-[(3R)-1-isobutylpyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (CDCl₃): δ 0.91 (d, J=6.60 Hz, 6H), 1.57 (m, 4H), 1.68 (m, 5H), 1.77(m, 6H), 2.21 (m, 2H), 2.27 (m, 1H), 2.35 (dd, J=9.30, 5.10 Hz, 1H),2.50 (t, J=6.00 Hz, 2H), 2.57 (m, 1H), 2.64 (t, J=6.50 Hz, 2H), 2.91(dd, J=9.30, 6.80 Hz, 1H), 3.63 (t, J=6.10 Hz, 4H), 4.40 (m, 1H), 6.09(m, 1H);

MS (ESI, Pos. 20 V): 372 (M+H)⁺, 186.5 (M+2H)²⁺;

TLC: Rf 0.45 (AcOEt:MeOH:TEA=20:2:1).

Example 14-284-azepan-1-yl-N-[(3S)-1-cyclohexylpyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.14 (m, 6H), 1.49 (m, 4H), 1.62 (m, 6H), 1.79 (m, 4H),1.99 (m, 2H), 2.29 (m, 1H), 2.55 (m, 5H), 2.86 (m, 3H), 3.60 (t, J=6.00Hz, 4H), 4.15 (m, 1H), 6.14 (m, 1H);

MS (ESI, Pos, 20 V): 384 (M+H)⁺, 302, 192.5 (M+2H)²⁺;

TLC: Rf 0.39 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-294-azepan-1-yl-N-[(3R)-1-cyclohexylpyrrolidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.15 (m, 6H), 1.46 (m, 4H), 1.66 (m, 10H), 1.82 (m,2H), 2.02 (m, 2H), 2.33 (m, 1H), 2.48 (m, 2H), 2.58 (m, 1H), 2.86 (m,3H), 3.61 (t, J=6.00 Hz, 4H), 4.17 (m, 1H), 6.12 (m, 1H);

MS (ESI, Pos. 20 V): 384 (M+H)⁺, 302;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 14-304-azepan-1-yl-N-[(3S)-1-cyclohexylpyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.17 (m, 6H), 1.63 (m, 16H), 1.99 (m, 2H), 2.28 (m,1H), 2.48 (m, 7H), 2.85 (t, J=8.00 Hz, 1H), 3.51 (t, J=6.00 Hz, 4H),4.15 (m, 1H), 6.14 (m, 1H);

MS (ESI, Pos, 20 V): 398 (M+H)⁺, 316, 199.5 (M+2H)²⁺;

TLC: Rf 0.39 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-314-azepan-1-yl-N-[(3R)-1-cyclohexylpyrrolidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.15 (m, 6H), 1.48 (m, 7H), 1.68 (m, 11H), 1.98 (m,2H), 2.29 (dd, J=9.10, 5.80 Hz, 1H), 2.45 (m, 5H), 2.85 (t, J=8.40 Hz,1H), 3.51 (t, J=6.00 Hz, 4H), 4.15 (m, 1H), 6.13 (m, 1H);

MS (ESI, Pos. 20 V): 398 (M+H)⁺, 316, 199.5 (M+2H)²⁺;

TLC: Rf 0.50 (AcOEt:MeOH:TEA=20:2:1).

Example 14-32 6-azepan-1-yl-N-(1-benzylpyrrolidin-3-yl)-9H-purin-2-amine

NMR (DMSO-d₆): δ 1.44 (m, 4H), 1.73 (m, 6H), 2.11 (m, 1H), 2.30 (dd,J=9.00, 5.20 Hz, 1H), 2.50 (m, 2H), 2.80 (dd, J=9.00, 7.00 Hz, 1H), 3.54(s, 2H), 3.80 (m, 2H), 4.25 (m, 2H), 6.13 (d, J=6.80 Hz, 1H), 7.23 (m,5H), 7.61 (s, 1H), 12.15 (m, 1H);

MS (LC-MS, APCI, Pos. 20 V): 392 (M+H)⁺;

TLC: Rf 0.40 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-334-azepan-1-yl-N-(1-cyclohexylpiperidin-3-yl)-5,7-dihydrofuro[3,4-d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.08 (m, 6H), 1.45 (m, 6H), 1.72 (m, 10H), 1.99 (m,1H), 2.27 (m, 2H), 2.66 (m, 1H), 2.97 (m, 1H), 3.50 (m, 4H), 3.78 (m,1H), 4.56 (s, 2H), 5.04 (s, 2H), 6.22 (m, 1H);

MS (ESI, Pos, 20 V): 400 (M+H)⁺, 318, 200.5 (M+2H)²⁺;

TLC: Rf 0.59 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-346-azepan-1-yl-2-[(1-cyclohexylpiperidin-3-yl)amino]pyrimidine-4-carboxylicacid dihydrochloride

NMR (CD₃OD): δ 1.23 (m, 2H), 1.39 (m, 3H), 1.63 (m, 6H), 1.86 (m, 6H),2.13 (m, 5H), 3.06 (m, 1H), 3.21 (m, 1H), 3.51 (m, 1H), 3.72 (m, 2H),3.79 (m, 2H), 4.01 (m, 1H), 4.06 (m, 1H), 4.56 (m, 1H), 6.98 (s, 1H);

MS (FAB, Pos., matrix=Glycerin+m-NBA): 402 (M+H)⁺, 237;

TLC: Rf 0.25 (AcOEt:MeOH:TEA=20:2:1).

Example 14-356-azepan-1-yl-2-[(1-benzylpiperidin-3-yl)amino]pyrimidine-4-carboxamide

NMR (CDCl₃): δ 1.52 (m, 6H), 1.74 (m, 6H), 2.20 (m, 1H), 2.36 (m, 1H),2.47 (m, 1H), 2.84 (m, 1H), 3.46 (d, J=13.20 Hz, 1H), 3.56 (d, J=13.20Hz, 1H), 3.68 (m, 4H), 4.04 (m, 1H), 5.04 (m, 1H), 5.48 (m, 1H), 6.65(s, 1H), 7.28 (m, 5H), 7.67 (m, 1H);

MS (ESI, Pos. 20 V): 409 (M+H)⁺, 319;

TLC: Rf 0.60 (CHCl₃:MeOH=10:1).

Example 14-366-azepan-1-yl-2-(piperidin-3-ylamino)pyrimidine-4-carboxamide

NMR (CDCl₃): δ 1.52 (m, 5H), 1.75 (m, 6H), 1.98 (m, 1H), 2.60 (m, 1H),2.74 (m, 1H), 2.90 (m, 1H), 2.99 (m, 1H), 3.36 (m, 1H), 3.50 (m, 2H),3.71 (m, 2H), 4.06 (m, 1H), 4.96 (d, J=7.50 Hz, 1H), 5.71 (m, 1H), 6.68(s, 1H), 7.89 (m, 1H);

MS (ESI, Pos. 20 V): 319 (M+H)⁺, 236, 160 (M+2H)²⁺;

TLC: Rf 0.20 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-376-azepan-1-yl-2-[(1-cyclohexylpiperidin-3-yl)amino]pyrimidine-4-carboxamide

NMR (CDCl₃): δ 1.22 (m, 6H), 1.53 (m, 6H), 1.76 (m, 10H), 2.27 (m, 2H),2.44 (m, 1H), 2.62 (m, 1H), 2.98 (m, 1H), 3.51 (m, 2H), 3.74 (m, 2H),4.01 (m, 1H), 5.04 (m, 1H), 5.47 (m, 1H), 6.66 (s, 1H), 7.77 (m, 1H);

MS (ESI, Pos. 20 V): 401 (M+H)⁺, 319, 201 (M+2H)²⁺;

TLC: Rf 0.28 (CHCl₃:MeOH=10:1).

Example 14-384-azepan-1-yl-N-[(3S)-1-benzylazepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.39 (m, 5H), 1.67 (m, 8H), 1.86 (m, 3H), 2.52 (m, 5H),2.83 (m, 3H), 3.57 (t, J=5.90 Hz, 4H), 3.62 (s, 2H), 3.96 (m, 1H), 5.83(m, 1H), 7.27 (m, 5H);

MS (ESI, Pos. 20 V): 839 (2M+H)⁺, 420 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.16;

TLC: Rf 0.42 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-394-azepan-1-yl-N-[(3R)-1-benzylazepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.42 (m, 6H), 1.60 (m, 8H), 1.84 (m, 2H), 2.51 (m, 5H),2.82 (m, 3H), 3.57 (t, J=6.00 Hz, 4H), 3.62 (s, 2H), 3.97 (m, 1H), 5.86(m, 1H), 7.25 (m, 5H);

MS (ESI, Pos. 20 V): 839 (2M+H)⁺, 420 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.18;

TLC: Rf 0.50 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-40N-[(3S)-azepan-3-yl]-4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.44 (m, 5H), 1.54 (m, 4H), 1.70 (m, 5H), 1.84 (m, 2H),2.49 (m, 2H), 2.58 (dd, J=13.60, 7.00 Hz, 1H), 2.71 (t, J=6.00 Hz, 2H),2.87 (m, 3H), 3.59 (t, J=6.00 Hz, 4H), 3.85 (m, 1H), 5.83 (m, 1H);

MS (ESI, Pos. 20 V): 330 (M+H)⁺, 165.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.03;

TLC: Rf 0.38 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-41N-[(3R)-azepan-3-yl]-4-azepan-1-yl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.45 (m, 5H), 1.54 (m, 4H), 1.68 (m, 5H), 1.84 (m, 2H),2.49 (m, 2H), 2.58 (dd, J=13.60, 7.10 Hz, 1H), 2.71 (t, J=5.90 Hz, 2H),2.87 (m, 3H), 3.59 (t, J=6.00 Hz, 4H), 3.86 (m, 1H), 5.86 (m, 1H);

MS (ESI, Pos. 20 V): 330 (M+H)⁺, 165.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05;

TLC: Rf 0.38 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-424-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)azepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amineExample 14-434-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)azepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amineExample 14-444-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)azepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 414 (M+H)⁺, 330, 207.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.25.

Example 14-454-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)azepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 414 (M+H)⁺, 330, 207.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 14-464-azepan-1-yl-N-[(3S)-1-isobutylazepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 386 (M+H)⁺, 330, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 14-474-azepan-1-yl-N-[(3R)-1-isobutylazepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 386 (M+H)⁺, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 14-484-azepan-1-yl-N-[(3S)-1-cyclohexylazepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 412 (M+H)⁺, 386, 330, 206.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 14-494-azepan-1-yl-N-[(3R)-1-cyclohexylazepan-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos. 20 V): 412 (M+H)⁺, 386, 330, 206.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 14-504-azepan-1-yl-N-[(3S)-1-benzylazepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.45 (m, 4H), 1.56 (m, 6H), 1.77 (m, 8H), 2.47 (m, 5H),2.79 (m, 1H), 3.16 (d, J=5.10 Hz, 2H), 3.48 (t, J=6.00 Hz, 4H), 3.62 (s,2H), 3.91 (m, 1H), 5.85 (m, 1H), 7.25 (m, 5H);

MS (ESI, Pos. 20 V): 434 (M+H)⁺, 344;

HPLC condition: A; HPLC retention time (min): 3.23;

TLC: Rf 0.42 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-514-azepan-1-yl-N-[(3R)-1-benzylazepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.45 (m, 4H), 1.56 (m, 6H), 1.75 (m, 8H), 2.47 (m, 5H),2.79 (dd, J=13.10, 3.90 Hz, 1H), 3.16 (d, J=5.00 Hz, 2H), 3.47 (t,J=6.00 Hz, 4H), 3.62 (s, 2H), 3.94 (m, 1H), 5.83 (m, 1H), 7.23 (m, 5H);

MS (ESI, Pos. 20 V): 434 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 3.23;

TLC: Rf 0.42 (CHCl₃:MeOH:NH₄OH=80:10:1)

Example 14-52N-[(3R)-azepan-3-yl]-4-azepan-1-yl-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.46 (m, 6H), 1.56 (m, 5H), 1.69 (m, 7H), 2.39 (m, 4H),2.56 (m, 1H), 2.71 (t, J=5.90 Hz, 2H), 2.88 (dd, J=13.50, 4.30 Hz, 1H),3.50 (t, J=6.00 Hz, 4H), 3.83 (m, 1H), 5.84 (m, 1H);

MS (ESI, Pos. 20 V): 344 (M+H)⁺, 172.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11;

TLC: Rf 0.38 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-534-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)azepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amineExample 14-544-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)azepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine Example 14-554-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)azepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos. 20 V): 428 (M+H)⁺, 344, 214.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.33.

Example 14-564-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)azepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos. 20 V): 428 (M+H)⁺, 344, 214.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.34.

Example 14-574-azepan-1-yl-N-[(3S)-1-isobutylazepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos. 20 V): 400 (M+H)⁺, 200.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 14-584-azepan-1-yl-N-[(3R)-1-isobutylazepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos. 20 V): 400 (M+H)⁺, 200.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 14-594-azepan-1-yl-N-[(3S)-1-cyclohexylazepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos. 20 V): 426 (M+H)⁺, 400, 344, 213.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 14-604-azepan-1-yl-N-[(3R)-1-cyclohexylazepan-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 426 (M+H)⁺, 400, 344, 213.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.27.

Example 14-614-azepan-1-yl-N-[(3S)-1-benzylpiperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 811 (2M+H)⁺, 406 (M+H)⁺, 316;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 14-624-azepan-1-yl-N-[(3R)-1-benzylpiperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 811 (2M+H)⁺, 406 (M+H)⁺, 316;

HPLC condition: A; HPLC retention time (min): 3.14.

Example 14-634-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)piperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 407 (M+H)⁺, 204 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 14-644-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)piperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 407 (M+H)⁺, 204 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.05.

Example 14-654-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)piperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 799 (2M+H)⁺, 400 (M+H)⁺, 200.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 14-664-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)piperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 799 (2M+H)⁺, 400 (M+H)⁺, 200.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.23.

Example 14-674-azepan-1-yl-N-[(3S)-1-isobutylpiperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 743 (2M+H)⁺, 372 (M+H)⁺, 316, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 14-684-azepan-1-yl-N-[(3R)-1-isobutylpiperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 743 (2M+H)⁺, 372 (M+H)⁺, 344, 186.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 14-694-azepan-1-yl-N-[(3S)-1-cyclohexylpiperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 398 (M+H)⁺, 372, 316, 199.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 14-704-azepan-1-yl-N-[(3R)-1-cyclohexylpiperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

MS (ESI, Pos.20V): 795 (2M+H)⁺, 398 (M+H)⁺, 199.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 14-714-azepan-1-yl-N-[(3S)-piperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (CDCl₃): δ 1.48 (m, 2H), 1.54 (m, 4H), 1.74 (m, 4H), 1.98 (m, 4H),2.52 (dd, J=11.70, 8.20 Hz, 1H), 2.62 (m, 1H), 2.67 (t, J=7.10 Hz, 2H),2.87 (m, 1H), 2.94 (t, J=7.10 Hz, 2H), 3.25 (dd, J=11.70, 3.70 Hz, 1H),3.67 (t, J=6.00 Hz, 4H), 3.84 (m, 1H), 4.82 (d, J=7.90 Hz, 1H);

MS (ESI, Pos. 20 V): 631 (2M+H)⁺, 316 (M+H)⁺, 158.5 (M+2H)²⁺;

TLC: Rf 0.17 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-724-azepan-1-yl-N-[(3R)-piperidin-3-yl]-6,7-dihydro-5H-cyclopenta[d]pyrimidin-2-amine

NMR (DMSO-d₆): δ 1.33 (m, 2H), 1.45 (m, 4H), 1.56 (m, 1H), 1.66 (m, 4H),1.83 (m, 3H), 2.31 (dd, J=11.40, 8.70 Hz, 1H), 2.41 (m, 3H), 2.73 (m,1H), 2.86 (t, J=7.10 Hz, 2H), 2.98 (dd, J=11.40, 3.70 Hz, 1H), 3.59 (t,J=6.00 Hz, 4H), 3.70 (m, 1H), 5.93 (m, 1H);

MS (ESI, Pos. 20 V): 316 (M+H)⁺, 158.5 (M+2H)²⁺;

TLC: Rf 0.17 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-734-azepan-1-yl-N-[(3S)-1-benzylpiperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 839 (2M+H)⁺, 420 (M+H)⁺, 330;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 14-744-azepan-1-yl-N-[(3R)-1-benzylpiperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 839 (2M+H)⁺, 420 (M+H)⁺, 330;

HPLC condition: A; HPLC retention time (min): 3.20.

Example 14-754-azepan-1-yl-N-[(3S)-1-(pyridin-2-ylmethyl)piperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 421 (M+H)⁺, 402, 330, 211 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 14-764-azepan-1-yl-N-[(3R)-1-(pyridin-2-ylmethyl)piperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 421 (M+H)⁺, 402, 330, 211 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.11.

Example 14-774-azepan-1-yl-N-[(3S)-1-(2-ethylbutyl)piperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 827 (2M+H)⁺, 414 (M+H)⁺, 330, 207.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 14-784-azepan-1-yl-N-[(3R)-1-(2-ethylbutyl)piperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 414 (M+H)⁺, 330, 207.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.29.

Example 14-794-azepan-1-yl-N-[(3S)-1-isobutylpiperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 771 (2M+H)⁺, 386 (M+H)⁺, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 14-804-azepan-1-yl-N-[(3R)-1-isobutylpiperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 771 (2M+H)⁺, 386 (M+H)⁺, 193.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.16.

Example 14-814-azepan-1-yl-N-[(3S)-1-cyclohexylpiperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 823 (2M+H)⁺, 412 (M+H)⁺, 330, 206.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 14-824-azepan-1-yl-N-[(3R)-1-cyclohexylpiperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

MS (ESI, Pos.20V): 823 (2M+H)⁺, 412 (M+H)⁺, 330, 206.5 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 3.22.

Example 14-834-azepan-1-yl-N-[(3S)-piperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (CDCl₃): δ 1.47 (m, 2H), 1.56 (m, 4H), 1.67 (m, 2H), 1.76 (m, 6H),1.99 (m, 2H), 2.49 (t, J=6.70 Hz, 2H), 2.53 (m, 1H), 2.61 (t, J=6.70 Hz,2H), 2.66 (m, 1H), 2.89 (m, 1H), 3.24 (dd, J=11.50, 3.50 Hz, 1H), 3.59(t, J=6.00 Hz, 4H), 3.81 (m, 1H), 4.88 (m, 1H);

MS (ESI, Pos. 20 V): 330 (M+H)⁺, 165.5 (M+2H)²⁺;

TLC: Rf 0.17 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 14-844-azepan-1-yl-N-[(3R)-piperidin-3-yl]-5,6,7,8-tetrahydroquinazolin-2-amine

NMR (DMSO-d₆): δ 1.35 (m, 2H), 1.49 (m, 4H), 1.58 (m, 3H), 1.67 (m, 6H),1.83 (m, 1H), 2.30 (dd, J=11.80, 8.80 Hz, 1H), 2.44 (m, 5H), 2.72 (m,1H), 2.97 (dd, J=11.80, 3.60 Hz, 1H), 3.50 (t, J=5.90 Hz, 4H), 3.63 (m,1H), 5.91 (m, 1H);

MS (ESI, Pos. 20 V): 330 (M+H)⁺, 165.5 (M+2H)²⁺;

TLC: Rf 0.17 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 15-01 to Example 15-55

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 15-01N²-(2-aminoethyl)-N⁴-benzyl-N⁴-methylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 258 (M+H);

HPLC condition: A; HPLC retention time (min): 2.89.

Example 15-02N²-(2-aminoethyl)-N⁴-methyl-N⁴-(2-phenylethyl)pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 272 (M+H);

HPLC condition: A; HPLC retention time (min): 2.95.

Example 15-03 N²-(2-aminoethyl)-N⁴,N⁴-diisopentylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 294 (M+H);

HPLC condition: A; HPLC retention time (min): 3.24.

Example 15-04N²-(2-aminoethyl)-N⁴-[3-(dimethylamino)propyl]-N⁴-methylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 253 (M+H);

HPLC condition: B; HPLC retention time (min): 2.83.

Example 15-051,1′-(2-[(2-aminoethyl)amino]-4-pyrimidinylimino)di(2-propanol) Example15-06 N²-(2-aminoethyl)-N⁴,N⁴-dibutylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 266 (M+H);

HPLC condition: A; HPLC retention time (min): 3.10.

Example 15-07N²-(2-aminoethyl)-N⁴-[2-(dimethylamino)ethyl]-N⁴-methylpyrimidine-2,4-diamineExample 15-082-[2-[(2-aminoethyl)amino]pyrimidin-4-yl(butyl)amino]ethanol

MS (ESI, Pos.20V): 254 (M+H);

HPLC condition: A;

HPLC retention time (min): 2.79.

Example 15-09N²-(2-aminoethyl)-N⁴,N⁴-bis(2-methoxyethyl)pyrimidine-2,4-diamineExample 15-10N²-(2-aminoethyl)-N⁴-methyl-N⁴-(2-pyridin-2-ylethyl)pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 273 (M+H);

HPLC condition: B; HPLC retention time (min): 2.86.

Example 15-11N²-(2-aminoethyl)-N⁴-methyl-N⁴-(1-methylpiperidin-4-yl)pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 265 (M+H);

HPLC condition: B; HPLC retention time (min): 2.81.

Example 15-12N²-(2-aminoethyl)-N⁴,N⁴-bis[3-(dimethylamino)propyl]pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 324 (M+H);

HPLC condition: B; HPLC retention time (min): 3.02.

Example 15-13 N²-(2-aminoethyl)-N⁴-(2-methoxyethyl)-N⁴-methylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 226 (M+H);

HPLC condition: B; HPLC retention time (min): 2.69.

Example 15-14N²-(2-aminoethyl)-N⁴-methyl-N⁴-(4-pyridin-3-ylbutyl)pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 301 (M+H);

HPLC condition: B; HPLC retention time (min): 3.14.

Example 15-15N²-(2-aminoethyl)-N⁴-methyl-N⁴-[(6-methylpyridin-2-yl)methyl]pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 273 (M+H);

HPLC condition: B; HPLC retention time (min): 2.92.

Example 15-16N²-(2-aminoethyl)-N⁴-benzyl-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 315 (M+H);

HPLC condition: A; HPLC retention time (min): 2.63.

Example 15-17N²-(2-aminoethyl)-N⁴-(2-furylmethyl)-N⁴-methylpyrimidine-2,4-diamineExample 15-184-[2-[(2-aminoethyl)amino]pyrimidin-4-yl(ethyl)amino]butan-1-ol Example15-19 N²-(2-aminoethyl)-N⁴,N⁴-bis(2-ethoxyethyl)pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 298 (M+H);

HPLC condition: A; HPLC retention time (min): 2.86.

Example 15-20 N²-(2-aminoethyl)-N⁴-cyclohexylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 236 (M+H);

HPLC condition: A; HPLC retention time (min): 2.88.

Example 15-21N²-(2-aminoethyl)-N⁴-[(5-methyl-2-furyl)methyl]pyrimidine-2,4-diamineExample 15-22N²-(2-aminoethyl)-N⁴-(2,3-dihydro-1H-inden-1-yl)pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 270 (M+H);

HPLC condition: A; HPLC retention time (min): 2.93.

Example 15-23N²-(2-aminoethyl)-N⁴-(pyridin-3-ylmethyl)pyrimidine-2,4-diamine Example15-24 N²-(2-aminoethyl)-N⁴-(2-piperidin-1-ylethyl)pyrimidine-2,4-diamine

MS (ESI, Pos.20V): 265 (M+H);

HPLC condition: B; HPLC retention time (min): 2.90.

Example 15-25 N²-(2-aminoethyl)-N⁴-benzylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 244 (M+H);

HPLC condition: A; HPLC retention time (min): 2.79.

Example 15-26 N²-(2-aminoethyl)-N⁴-cyclooctylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 264 (M+H);

HPLC condition: A; HPLC retention time (min): 3.02.

Example 15-27 N²-(2-aminoethyl)-N⁴-hexylpyrimidine-2,4-diamine

MS (ESI, Pos.20V): 238 (M+H);

HPLC condition: A; HPLC retention time (min): 2.99.

Example 15-28N²-(2-aminoethyl)-N⁴-methyl-N⁴-phenylpyrimidine-2,4-diaminedihydrochloride

NMR (CD₃OD): δ 7.66-7.44 (m, 4H), 7.41-7.32 (m, 2H), 5.82 (d, J=7.5 Hz,1H), 3.87 (t, J=6.0 Hz, 2H), 3.60 (s, 3H), 3.30 (t, J=6.0 Hz, 2H);

MS (FAB, Pos., Glycerin+m-NBA): 244 (M+H)⁺, 227, 201;

TLC: Rf 0.20 (n-BuOH:AcOH:H₂O=4:2:1).

Example 15-29N²-(2-aminoethyl)-N⁴-benzyl-N⁴-phenylpyrimidine-2,4-diaminedihydrochloride

NMR (CD₃OD): δ 7.67 (d, J=7.2 Hz, 1H), 7.54-7.39 (m, 3H), 7.37-7.17 (m,7H), 5.84 (d, J=7.2 Hz, 1H), 5.34 (s, 2H), 3.77 (t, J=6.0 Hz, 2H), 3.10(t, J=6.0 Hz, 2H);

MS (FAB, Pos., Glycerin+m-NBA): 320 (M+H)⁺, 303, 230;

TLC: Rf 0.26 (n-BuOH:AcOH:H₂O=4:2:1).

Example 15-30N²-(2-aminoethyl)-N⁴-(2-piperidin-1-ylethyl)pyrimidine-2,4-diaminedihydrochloride

NMR (DMSO-d₆): δ 1.39 (m, 1H), 1.79 (m, 5H), 2.95 (m, 4H), 3.24 (m, 2H),3.48 (m, 2H), 3.71 (m, 2H), 3.94 (m, 2H), 6.17 (d, J=7.30 Hz, 1H), 7.74(d, J=7.30 Hz, 1H), 8.43 (m, 4H), 9.51 (m, 1H), 10.75 (m, 1H) 12.70 (m,1H);

MS (LC-MS, APCI, Pos. 20 V): 265 (M+H)⁺;

TLC: Rf 0.38 (CHCl₃:MeOH:NH₄OH=80:20:4).

Example 15-312-[(4-[2-(dimethylamino)ethyl]aminopyrimidin-2-yl)(methyl)amino]ethanol

MS (ESI, Pos, 20 V): 240 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 2.72.

Example 15-32N⁴-[2-(dimethylamino)ethyl]-N²-methyl-N²-(1-naphthylmethyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 336 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.68.

Example 15-33N⁴-[2-(dimethylamino)ethyl]-N²-hexyl-N²-methylpyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 280 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.82.

Example 15-34N²-benzyl-N⁴-[2-(dimethylamino)ethyl]-N²-ethylpyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 300 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.62.

Example 15-35N²-benzyl-N⁴-[2-(dimethylamino)ethyl]-N²-methylpyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 286 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.45.

Example 15-36N⁴-[2-(dimethylamino)ethyl]-N²,N²-bis(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 364 (M+H)⁺, 214

HPLC condition: B; HPLC retention time (min): 3.05.

Example 15-37N⁴-[2-(dimethylamino)ethyl]-N²-methyl-N²-(1-methylpiperidin-4-yl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 293 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 2.98.

Example 15-38N²,N⁴-bis[2-(dimethylamino)ethyl]-N²-methylpyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 267 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 2.96.

Example 15-39N⁴-[2-(dimethylamino)ethyl]-N²-methyl-N²-(2-phenylethyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 300 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.56.

Example 15-40N⁴-[2-(dimethylamino)ethyl]-N²-(2-furylmethyl)-N²-methylpyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 276 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.29.

Example 15-41N⁴-[2-(dimethylamino)ethyl]-N²-[2-(1H-indol-3-yl)ethyl]-N²-methylpyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 339 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.47.

Example 15-42N²-cyclopentyl-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 250 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.22.

Example 15-43N²-cyclohexyl-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 527 (2M+H)⁺, 264 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.36.

Example 15-44N⁴-[2-(dimethylamino)ethyl]-N²-(3-methylcyclohexyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 555 (2M+H)⁺, 278 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.53.

Example 15-45N⁴-[2-(dimethylamino)ethyl]-N²-(4-methylcyclohexyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 555 (2M+H)⁺, 278 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.55.

Example 15-46N²-(cyclohexylmethyl)-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 555 (2M+H)⁺, 278 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.53.

Example 15-47N²-(2,3-dihydro-1H-inden-1-yl)-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 595 (2M+H)⁺, 298 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.42.

Example 15-48N²-cyclohexyl-N⁴-[2-(dimethylamino)ethyl]-N²-methylpyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 278 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.64.

Example 15-49N²-cycloheptyl-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 555 (2M+H)⁺, 278 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.55.

Example 15-50N⁴-[2-(dimethylamino)ethyl]-N²-(pyridin-3-ylmethyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 273 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 2.79.

Example 15-51N⁴-[2-(dimethylamino)ethyl]-N²-(pyridin-4-ylmethyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 273 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 2.78.

Example 15-52N²-benzyl-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 543 (2M+H)⁺, 272 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.23.

Example 15-53N⁴-[2-(dimethylamino)ethyl]-N²-(2-phenylethyl)pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 571 (2M+H)⁺, 286 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.34.

Example 15-54 N²-butyl-N⁴-[2-(dimethylamino)ethyl]pyrimidine-2,4-diamine

MS (ESI, Pos, 20 V): 238 (M+H)⁺;

HPLC condition: B; HPLC retention time (min): 3.20.

Example 15-556-(2-[(1-cyclohexylpiperidin-3-yl)amino]pyrimidin-4-ylamino)hexan-1-ol

NMR (DMSO-d₆): δ 1.17 (m, 6H), 1.29 (m, 5H), 1.48 (m, 6H), 1.72 (m, 5H),2.00 (m, 1H), 2.27 (m, 2H), 2.63 (m, 1H), 2.91 (m, 1H), 3.16 (m, 2H),3.41 (m, 2H), 3.76 (m, 1H), 4.36 (m, 1H), 5.65 (d, J=5.70 Hz, 1H), 6.03(m, 1H), 6.83 (m, 1H), 7.58 (d, J=5.70 Hz, 1H);

MS (ESI, Pos, 20 V): 376 (M+H)⁺, 294, 188.5 (M+2H)²⁺;

TLC: Rf 0.38 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 16-1 to Example 16-3

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 16-1 N,N′-bis[2-(dimethylamino)ethyl]quinazoline-2,4-diamine

MS (ESI, Pos. 20 V): 303 (M+H)⁺, 168;

HPLC condition: A; HPLC retention time (min): 0.36.

Example 16-2 N,N′-bis(2-pyrrolidin-1-ylethyl)quinazoline-2,4-diamine

MS (ESI, Pos. 20 V): 355 (M+H)⁺, 178 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.59.

Example 16-3 N,N′-bis(2-piperidin-1-ylethyl)quinazoline-2,4-diamine

MS (ESI, Pos. 20 V): 383 (M+H)⁺, 192 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.68.

Example 17-01 to Example 17-12

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 17-01N-(4-azepan-1-ylpyrimidin-2-yl)-N-[2-(dimethylamino)ethyl]-1,1′-biphenyl-4-carboxamide

MS (ESI, Pos.20V): 444 (M+H);

HPLC condition: A; HPLC retention time (min): 3.45.

Example 17-02N-(4-azepan-1-ylpyrimidin-2-yl)-N-[3-(dimethylamino)propyl]-1,1′-biphenyl-4-carboxamide

MS (ESI, Pos.20V): 458 (M+H);

HPLC condition: A; HPLC retention time (min): 3.29.

Example 17-03N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N-[2-(dimethylamino)ethyl]-1,1′-biphenyl-4-carboxamide

MS (ESI, Pos.20V): 478 (M+H);

HPLC condition: A; HPLC retention time (min): 3.54.

Example 17-04N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N-[3-(dimethylamino)propyl]-1,1′-biphenyl-4-carboxamide

MS (ESI, Pos.20V): 492 (M+H);

HPLC condition: A; HPLC retention time (min): 3.44.

Example 17-05N-[2-(dimethylamino)ethyl]-4-(pentyloxy)-N-(4-piperidin-1-ylpyrimidin-2-yl)benzamide

MS (ESI, Pos.20V): 440 (M+H);

HPLC condition: A; HPLC retention time (min): 3.47.

Example 17-06N-[3-(dimethylamino)propyl]-4-(pentyloxy)-N-(4-piperidin-1-ylpyrimidin-2-yl)benzamide

MS (ESI, Pos.20V): 454 (M+H);

HPLC condition: A; HPLC retention time (min): 3.36.

Example 17-07N-(4-azepan-1-ylpyrimidin-2-yl)-N-[2-(dimethylamino)ethyl]-4-(pentyloxy)benzamide

MS (ESI, Pos.20V): 454 (M+H);

HPLC condition: A; HPLC retention time (min): 3.52.

Example 17-08N-(4-azepan-1-ylpyrimidin-2-yl)-N-[3-(dimethylamino)propyl]-4-(pentyloxy)benzamide

MS (ESI, Pos.20V): 468 (M+H);

HPLC condition: A; HPLC retention time (min): 3.39.

Example 17-09N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N-[2-(dimethylamino)ethyl]-4-(pentyloxy)benzamide

MS (ESI, Pos.20V): 488 (M+H);

HPLC condition: A; HPLC retention time (min): 3.66.

Example 17-10N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N-[3-(dimethylamino)propyl]-4-(pentyloxy)benzamide

MS (ESI, Pos.20V): 502 (M+H);

HPLC condition: A; HPLC retention time (min): 3.55.

Example 17-113-cyclopentyl-N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N-[2-(dimethylamino)ethyl]propanamide

MS (ESI, Pos.20V): 422 (M+H);

HPLC condition: A; HPLC retention time (min): 3.46.

Example 17-123-cyclopentyl-N-[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-yl]-N-[3-(dimethylamino)propyl]propanamide

MS (ESI, Pos.20V): 436 (M+H);

HPLC condition: A; HPLC retention time (min): 3.26.

Example 18-1 to Example 18-3

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 18-12-[(4-azepan-1-ylquinazolin-2-yl)oxy]-N,N-dimethylethanamine

MS (ESI, Pos. 20 V): 315 (M+H)⁺;

HPLC condition: A; HPLC retention time (min): 2.83.

Example 18-24-azepan-1-yl-N-(1-cyclohexylpiperidin-3-yl)pyrimidine-2-carboxamide

NMR (CDCl₃): δ 1.22 (m, 4H), 1.58 (m, 8H), 1.82 (m, 10H), 2.30 (m, 1H),2.43 (m, 1H), 2.68 (m, 3H), 3.52 (m, 2H), 3.89 (m, 2H), 4.24 (m, 1H),6.45 (d, J=6.21 Hz, 1H), 8.28 (d, J=6.21 Hz, 1H), 8.58 (d, J=7.72 Hz,1H);

MS (ESI, Pos. 20 V): 386 (M+H)⁺;

TLC: Rf 0.53 (CHCl₃:MeOH=9:1).

Example 18-3 N-(4-azepan-1-yl-1-oxidopyrimidin-2-yl)ethane-1,2-diamine

NMR (CDCl₃): δ 1.54 (m, 4H), 1.76 (m, 4H), 1.98 (m, 2H), 2.94 (t, J=6.00Hz, 2H), 3.52 (q, J=6.00 Hz, 2H), 3.57 (m, 4H), 5.76 (d, J=7.30 Hz, 1H),7.26 (m, 1H), 7.84 (d, J=7.30 Hz, 1H);

MS (ESI, Pos. 20 V): 503 (2M+H)⁺, 252 (M+H)⁺, 126.5 (M+2H)²⁺;

TLC: Rf 0.13 (CHCl₃:MeOH:NH₄OH=40:10:1).

Example 19-01 to Example 19-12

By the same procedure as described in Reference Example 1→Example 1using corresponding compounds, the compounds of the present inventionhaving the following physical data were given.

Example 19-016-azepan-1-yl-N-(1-cyclohexylpiperidin-3-yl)pyridine-2-carboxamide

NMR (CDCl₃): δ 1.22 (m, 4H), 1.68 (m, 18H), 2.28 (m, 1H), 2.41 (m, 1H),2.67 (m, 3H), 3.65 (m, 4H), 4.20 (m, 1H), 6.61 (dd, J=8.56, 0.67 Hz,1H), 7.39 (dd, J=7.22, 0.67 Hz, 1H), 7.53 (dd, J=8.56, 7.22 Hz, 1H),8.65 (d, J=8.06 Hz, 1H);

MS (ESI, Pos. 20 V): 385 (M+H)⁺, 193 (M+2H)²⁺;

TLC: Rf 0.62 (CHCl₃:MeOH=9:1).

Example 19-02 N¹-(6-azepan-1-ylpyridin-2-yl)-N²,N²-dimethylglycinamide

NMR (CDCl₃): δ 1.54 (m, 4H), 1.77 (m, 4H), 2.37 (s, 6H), 3.06 (s, 2H),3.60 (t, J=6.04 Hz, 4H), 6.23 (dd, J=7.81, 0.84 Hz, 1H), 7.38 (dd,J=7.81, 0.84 Hz, 1H), 7.43 (t, J=7.81 Hz, 1H), 9.09 (s, 1H);

MS (ESI, Pos. 20 V): 277 (M+H)⁺;

TLC: Rf 0.76 (EtOAc:MeOH=9:1).

Example 19-03N¹-(4-azepan-1-ylquinolin-2-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 7.74 (d, J=7.5 Hz, 1H), 7.43-7.33 (m, 2H), 7.05 (m,1H), 6.51 (t, J=5.1 Hz, 1H), 6.28 (s, 1H), 3.43 (dt, J=5.1, 6.3 Hz, 2H),3.27 (m, 4H), 2.42 (t, J=6.3 Hz, 2H), 2.18 (s, 6H), 1.82 (m, 4H), 1.69(m, 4H);

MS (ESI, Pos. 20 V): 313 (M+H)⁺, 157 (M+2H)²⁺;

TLC: Rf 0.19 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 19-04N¹-(2-azepan-1-ylquinolin-4-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 7.80 (d, J=8.1 Hz, 1H), 7.33 (m, 2H), 6.99 (m, 1H),6.46 (t, J=5.1 Hz, 1H), 5.81 (s, 1H), 3.69 (t, J=6.0 Hz, 4H), 3.31 (m,2H), 2.53 (t, J=6.9 Hz, 2H), 2.21 (s, 6H), 1.74 (m, 4H), 1.47 (m, 4H);

MS (ESI, Pos. 20 V): 313 (M+H)⁺, 241, 157 (M+2H)²⁺;

TLC: Rf 0.22 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 19-05N¹-(1-azepan-1-ylisoquinolin-3-yl)-N²,N²-dimethylglycinamide

NMR (DMSO-d₆): δ 9.33 (s, 1H), 7.98 (d, J=8.7 Hz, 1H), 7.81 (s, 1H),7.70 (d, J=8.4 Hz, 1H), 7.54 (dd, J=8.4, 6.6 Hz, 1H), 7.33 (dd, J=8.7,6.6 Hz, 1H), 3.65 (m, 4H), 3.10 (s, 2H), 2.30 (s, 6H), 1.84 (m, 4H),1.64 (m, 4H);

MS (ESI, Pos, 20 V): 327 (M+H)⁺, 242, 164;

TLC: Rf 0.48 (CHCl₃:MeOH=10:1).

Example 19-06N¹-(1-azepan-1-ylisoquinolin-3-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 7.78 (d, J=8.4 Hz, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.29(dd, J=7.8, 6.6 Hz, 1H), 6.95 (dd, J=8.4, 6.6 Hz, 1H), 6.00 (s, 1H),5.64 (t, J=5.4 Hz, 1H), 3.95 (m, 4H), 3.25 (dt, J=5.4, 6.3 Hz, 2H), 2.42(t, J=6.3 Hz, 2H), 2.17 (s, 6H), 1.82 (m, 4H), 1.63 (m, 4H);

MS (ESI, Pos. 20 V): 313 (M+H)⁺, 157 (M+2H)²⁺;

HPLC condition: A; HPLC retention time (min): 2.85;

TLC: Rf 0.48 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 19-07 1-(4-azepan-1-yl-6-chloro-1,3,5-triazin-2-yl)azepane

NMR (DMSO-d₆): δ 1.46 (m, 8H), 1.65 (m, 8H), 3.61 (q, J=5.95 Hz, 8H);

MS (ESI, Pos. 20 V): 312, 310 (M+H)⁺;

TLC: Rf 0.77 (Hexane:AcOEt=3:1).

Example 19-08 N-(4-azepan-1-yl-1,3,5-triazin-2-yl)ethane-1,2-diaminedihydrochloride

NMR (DMSO-d₆): δ 1.49 (m, 4H), 1.73 (m, 4H), 3.00 (m, 2H), 3.63 (q,J=6.00 Hz, 2H), 3.77 (m, 4H), 8.26 (m, 2H), 8.41 (s, 1H), 8.69 (m, 1H);

MS (ESI, Pos, 20 V): 237 (M+H)⁺;

TLC: Rf 0.17 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 19-09N-(4-azepan-1-yl-6-chloro-1,3,5-triazin-2-yl)ethane-1,2-diaminedihydrochloride

NMR (CD₃OD): δ 1.60 (m, 4H), 1.80 (m, 4H), 3.21 (t, J=5.77 Hz, 2H), 3.79(m, 6H);

MS (ESI, Pos, 20 V): 273, 271 (M+H)⁺;

TLC: Rf 0.23 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 19-10N-(4-azepan-1-yl-6-methoxy-1,3,5-triazin-2-yl)ethane-1,2-diaminedihydrochloride

NMR (CD₃OD): δ 1.62 (m, 4H), 1.85 (m, 4H), 3.22 (t, J=6.00 Hz, 2H), 3.77(t, J=6.00 Hz, 2H), 3.87 (m, 4H), 4.11 (s, 3H);

MS (ESI, Pos, 20 V): 267 (M+H)⁺;

TLC: Rf 0.27 (CHCl₃:MeOH:NH₄OH=80:10:1).

Example 19-11 N-[5-(azepan-1-ylmethyl)pyrimidin-2-yl]ethane-1,2-diaminetrihydrochloride

NMR (DMSO-d₆): δ 1.59 (m, 4H), 1.81 (m, 4H), 2.98 (m, 4H), 3.27 (m, 2H),3.57 (m, 2H), 4.16 (d, J=5.10 Hz, 2H), 7.86 (m, 1H), 8.22 (m, 3H), 8.61(s, 2H), 11.22 (m, 1H);

MS (LC-MS, APCI, Pos. 20 V): 250 (M+H)⁺, 151;

TLC: Rf 0.46 (CHCl₃:MeOH:NH₄OH=80:20:4).

Example 19-12N¹-(4-cycloheptylquinazolin-2-yl)-N²,N²-dimethylethane-1,2-diamine

NMR (DMSO-d₆): δ 7.97 (d, J=8.1 Hz, 1H), 7.61 (m, 1H), 7.42 (d, J=6.9Hz, 1H), 7.17 (m, 1H), 6.85 (m, 1H), 3.62 (m, 1H), 3.43 (dt, J=6.0, 6.6Hz, 2H), 2.44 (t, J=6.6 Hz, 2H), 2.18 (s, 6H), 2.00-1.57 (m, 12H);

MS (ESI, Pos. 20 V): 313 (M+H)⁺, 157 (M+2H)²¹, 102;

TLC: Rf 0.46 (CHCl₃:MeOH:NH₄OH=80:10:1).

Biological Examples

An effectiveness of the compounds of the present invention representedby formulae (I) and (II) was confirmed, for example, by the followingexperiments. The entire procedure utilized a standard method togetherwith a cell exhibiting a high expression prepared in accordance with abasic gene engineering technology. A measurement method of the presentinvention has improved measurement accuracy and/or measurementsensitivity in order to evaluate the compounds of the present invention.The experimental method is detailed below.

As described above, in order to screen for a compound which inhibits thebinding of HIV with CXCR4 or CCR5 which is a receptor on a CD4 positivecell, an experiment in an assay system employing an HIV virus is a moredirect procedure. However, use of an HIV virus in a large scalescreening is not practical because of its difficulty in handling. On theother hand, since both of a T cell-directing (X4) HIV-1 and SDF-1 bindto CXCR4, there may be a certain common profile in the CXCR4 bindingsite on both of HIV and SDF-1 as well as in SDF-1 and HIV binding siteson the CXCR4. Accordingly, an assay system employing an SDF-1 which isan intrinsic ligand of CXCR4 instead of HIV can be utilized in order toidentify a compound which inhibits the adsorption of an HIV virus onto acell which is an action mechanism different from that of an existingAIDS drug (reverse transferase inhibitor or protease inhibitor).

Typically, as an assay for screening for a compound which inhibits thebinding between SDF-1 and CXCR4, a system measuring the binding betweenan I-labeled SDF-1 and a human T cell line known to express CXCR4 can beemployed. Since both of a macrophage (R5) HIV and RANTES, MIP-1α, MIP-1βbind to CCR5, a similar understanding is possible.

Experimental Methods Experiment Example 1 Inhibition of Human SDF-1 withCEM Cell

In a binding buffer solution (HEPES containing BSA), a human T cell lineCEM cell was mixed with a test compound and ¹²⁵I-SDF-1 (NEN) andincubated for 60 minutes at 40° C. The reacted CEM cell was filteredrapidly through a GF/B membrane filter plate (Packard) to effectadsorption, followed by washing three times with PBS, drying andaddition of Microscint+20 (Packard). The radioactivity binding to theCEM cell is measured using Top Count (Packard) and a % inhibition by atest compound was calculated according to the equation shown below.

% Inhibition=(Et−Ea)/(Et−Ec)×100

-   -   Et: Radioactivity in the absence of a test compound    -   Ec: Radioactivity in the presence of non-radioactive SDF-1        (Pepro Tech) as a test compound at a level 1000 times higher        than ¹²⁵I-SDF-1    -   Ea: Radioactivity in the presence of a test compound

All compounds of the present invention described in Examples exhibitedinhibitions of 50% or higher at 10 μM. For example, the IC₅₀ values ofthe compounds of Example 1(41) and Example 4 are 0.20 μM and 0.15 μM,respectively.

Formulation Example 1

Each of the following components was mixed by a standard method andpunched out to give 10000 tablets each containing 10 mg of activeingredient.

2-(2-dimethylaminoethylamino)-4-(perhydroazepin-1- 5.0 g yl)pyrimidinecarcium carboxymethyl cellulose (disintegrant) 20.0 g magnesium stearate(lubricant) 10.0 g microcrystalline cellulose 870 g

Formulation example 2

Each of the following components was mixed by a standard method andfiltered through a dustproofing filter, and then 5 ml aliquots werecharged into ampoules, which were autoclaved to thereby obtain 10,000ampoules each containing 20 mg of the active ingredient.

2-(2-dimethylaminoethylamino)-4-(perhydroazepin-1- 200 g yl)pyrimidinemannitol 2 kg distilled water 50 L

1. A compound represented by formula (I):

wherein ring A represents a nitrogen-containing heterocyclic group whichmay have a substituent(s); ring B represents a homocyclic group whichmay have a substituent(s) or a heterocyclic group which may have asubstituent(s); and Y represents a hydrocarbon group which may have asubstituent(s), a heterocyclic group which may have a substituent(s), anamino group which may be protected, a hydroxyl group which may beprotected or a mercapto group which may be protected, a salt thereof, anN-oxide thereof, a solvate thereof, or a prodrug thereof.
 2. Thecompound according to claim 1, wherein ring A is a 5- to 10-memberednitrogen-containing heterocyclic group which may have a substituent(s).3. The compound according to claim 1, wherein ring B is anitrogen-containing heterocyclic group which may have a substituent(s).4. The compound according to claim 1, wherein Y is

wherein G represents a bond or a spacer containing 1 to 3 atoms as amain chain; ring J represents a 4- to 7-membered nitrogen-containingheterocyclic group which may have a substituent(s); and W representshydrogen, a hydrocarbon group which may have a substituent(s) or aheterocyclic group which may have a substituent(s).
 5. The compoundaccording to claim 1, which is represented by formula (I-1):

wherein ring A¹ represents a 5- to 10-membered nitrogen-containingsaturated heterocyclic group which may have a substituent(s), or a 5- to10-membered nitrogen-containing heterocyclic group which has one doublebond and which may have a substituent(s); ring B¹ represents a 6- to11-membered nitrogen-containing monocyclic or bicyclic heterocyclicgroup which may have a substituent(s); and other symbols have the samemeanings as those described in claim
 4. 6. The compound according toclaim 1, which is represented by formula (I-2):

wherein all symbols have the same meanings as those described in claim 1or
 4. 7. A compound represented by formula (I-A):

wherein ring A^(A) represents a 4- to 15-membered monocyclic, bicyclicor tricyclic heterocyclic group which is saturated or has one doublebond and which contains at least one nitrogen atom and may furthercontain 1 to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfuratom; ring B^(A) represents B^(A1) or B^(A2); B^(A1) represents:

B^(A2) represents:

R⁴ represents (i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenyl or C2-15alkynyl which may be substituted with 1 to 5 of R¹⁰, (iii) a C3-8carbocyclic group which may be substituted with 1 to 5 of R³, (iv) a 5-to 15-membered heterocyclic group which contains 1 or 2 nitrogen atoms,1 or 2 oxygen atoms and/or one sulfur atom and which may be substitutedwith 1 to 5 of R³, (v) COR⁵ wherein R⁵ represents C1-15 alkyl, C2-15alkenyl, C2-15 alkynyl or phenyl, or (vi) COOR⁶ wherein R⁶ representsC1-15 alkyl, C2-15 alkenyl, C2-15 alkynyl or phenyl; the upward arrowrepresents a binding position to ring A^(A); and the right-downwardarrow represents a binding position to the nitrogen atom bound to L; Lrepresents (1) a bond, (2) C1-8 alkylene, C2-8 alkenylene or C2-8alkynylene, wherein the alkylene, alkenylene and alkynylene each may besubstituted with 1 to 5 of R¹⁰, or (3) a C3-8 carbocyclic group whichmay be substituted with R³; Q represents (1) NR¹R² wherein R¹ and R²each independently represents (i) hydrogen, (ii) C1-15 alkyl, C2-15alkenyl or C2-15 alkynyl which may be substituted with 1 to 5 of R¹⁰,(iii) a C3-8 carbocyclic group which may be substituted with 1 to 5 ofR³, or (iv) a 5- to 15-membered heterocyclic group which contains 1 or 2nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfur atom and which maybe substituted 1 to 5 of R³, or (2) ring C; ring C represents a 4- to15-membered heterocyclic group which contains at least one nitrogen atomand may further contain 1 or 2 nitrogen atoms, 1 or 2 oxygen atomsand/or one sulfur atom and which may be substituted with 1 to 5 of R³;plural R³'s each independently represents (1) C1-15 alkyl, C2-15 alkenylor C2-15 alkynyl, wherein the alkyl, alkenyl and alkynyl may besubstituted with 1 to 5 of R¹⁰, (2) oxo, or (3)R¹⁰; plural R¹⁰'s eachindependently represents (1) OR¹¹, (2) OCOR¹², (3) OCOOR¹³, (4) NR¹⁴R¹⁵,(5) NR¹⁶COR¹², (6) NR¹⁶CONR¹⁴R¹⁵, (7) NR¹⁶COOR¹³, (8) COOR¹³, (9) COR¹²,(10) CONR¹⁴R¹⁵, (11) SO₂R¹², (12) SOR²², (13) SO₂NR²⁴R²⁵, (14)NR¹⁶SO₂R¹², (15) B(OH)₂, (16) SR¹¹, (17) halogen, (18) nitro, (19)cyano, or (20) ring D; R¹¹ represents (i) hydrogen, (ii) C1-15 alkyl,C2-15 alkenyl or C2-15 alkynyl, wherein the alkyl, alkenyl and alkynylmay be substituted with 1 to 5 of halogen, NR¹⁴R¹⁵, OR²¹, SR²¹, COOR¹³,or ring D, or (iii) ring D; R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ eachindependently represents (i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenylor C2-15 alkynyl which may be substituted with ring D, or (iii) ring D;ring D represents a C3-15 monocyclic, bicyclic or tricyclic carbocyclicgroup, or a 5- to 15-membered monocyclic, bicyclic or tricyclicheterocyclic group which contains 1 to 4 nitrogen atoms, 1 or 2 oxygenatoms and/or one sulfur atom; and ring D may be substituted with 1 to 5of the groups selected from the following (1) to (22): (1) C1-15 alkyl,C2-15 alkenyl or C2-15 alkynyl, wherein the alkyl, alkenyl or alkynylmay be substituted with 1 to 5 of OR²¹, OCOR²², OCOOR²³, NR²⁴R²⁵,NR²⁶COR²², NR²⁶CONR²⁴R²⁵, NR²⁶COOR²³, COOR²³, COR²², CONR²⁴R²⁵, SO₂R²²,SOR²², SO₂NR²⁴R²⁵, NR²⁶SO₂R²², B(OH)₂, SR²¹, halogen, nitro or cyano,(2) oxo, (3) OR²¹, (4) OCOR²², (5) OCOOR²³, (6) NR²⁴R²⁵, (7) NR²⁶COR²²,(8) NR²⁶CONR²⁴R²⁵, (9) NR²⁶COOR²³, (10) COOR²³, (11) COR²², (12)CONR²⁴R²⁵, (13) SO₂R²², (14) SOR²², (15) SO₂NR²⁴R²⁵, (16) NR²⁶SO₂R²²,(17) B(OH)₂, (18) SR²¹, (19) halogen, (20) nitro, (21) cyano or (22)ring E; R²¹ represents (i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenyl orC2-15 alkynyl which may be substituted with COR²², NR²⁴R²⁵ or ring E, or(iii) ring E; R²², R²³, R²⁴, R²⁵ and R²⁶ each independently represents(i) hydrogen, (ii) C1-15 alkyl, C2-15 alkenyl or C2-15 alkynyl which maybe substituted with ring E, or (iii) ring E; ring E represents a C3-15monocyclic, bicyclic or tricyclic carbocyclic group, or a 5- to15-membered monocyclic, bicyclic or tricyclic heterocyclic group whichcontains 1 to 4 nitrogen atoms, 1 or 2 oxygen atoms and/or one sulfuratom, and ring E may be substituted with 1 to 5 of (i) C1-15 alkyl whichmay be substituted with phenyl, (ii) halogen, (iii) phenyl, (iv) C1-15alkoxy, (v) hydroxyl, (vi) amino, (vii) mono(C1-8 alkyl)amino, or (viii)di(C1-8 alkyl)amino; ring A^(A) may be substituted with 1-5 of R^(a);ring B^(A) may be substituted with 1-5 of R^(b); R^(a) and R^(b) eachindependently represents a group which has the same meaning as the grouprepresented by R³; and wherein the following compounds (1) to (6) areexcluded: (1) N-[4-(4-morpholinyl)-2-quinazolinyl]-1,2-ethanediaminedihydrochloride, (2)N,N-dimethyl-N′42-(4-phenyl-1-piperidinyl)-4-pyrimidinyl]-1,2-ethylenediamine,(3)N-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-N′-[2-(1-piperidinyl)-4-pyrimidinyl]-1,3-propanediamine,(4)N-[(3,4-dihydro-2H-1-benzopyrane-2-yl)methyl]-N′-[2-(1-piperidinyl)-4-pyrimidinyl]-1,3-propanediamineoxalate, (5)N,N-diethyl-N′-[2-(1-pyrrolidinyl)-4-quinazolinyl-1,2-ethanediamine, and(6) N,N-diethyl-N′-[2-(1-pyrrolidinyl)-4-quinazolinyl-1,2-ethanediaminedihydrochloride, a salt thereof, an N-oxide thereof, a solvate thereof,or a prodrug thereof.
 8. A Compound represented by formula (I-B):

wherein ring A^(B) represents a 7- to 15-membered monocyclic, bicyclicor tricyclic heterocyclic group which is saturated or contains onedouble bond and which contains at least one nitrogen atom and mayfurther contain 1 to 3 nitrogen atoms, 1 or 2 oxygen atoms and/or onesulfur atom; ring B^(B) represents:

wherein ring Z represents a C5-10 monocyclic or bicyclic carbocyclicgroup, or a 5- to 10-membered monocyclic or bicyclic heterocyclic groupwhich may contain 1 or 2 nitrogen atoms, one oxygen atom and/or onesulfur atom; the upward arrow represents a binding position to ringA^(B); and the right-downward arrow represents a binding position to thenitrogen atom bound to L; ring A^(B) may be substituted with 1 to 5 ofR^(a); ring B^(B) may be substituted with 1 to 5 of R^(b); and R^(a),R^(b) and other symbols have the same meanings as those described inclaim 7, and wherein the following compounds (1) to (7) are excluded:(1)N-[4-(hexahydro-1H-azepin-1-yl)thieno[3,2-d.]pyrimidin-2-yl]-1,4-butandiaminedihydrochloride, (2)7-[4-[4,6-bis(hexahydro-1H-azepin-1-yl)-1,3,5-triazin-2-yl]amino-2H-1,2,3-triazol-2-yl]-3-phenyl-2H-1-benzopyran-2-one,(3)4-ethoxy-6-(hexahydro-1H-azepin-1-yl)-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine,(4)4-(hexahydro-1H-azepin-1-yl)-6-methyl-N-[3-(4-morpholinyl)propyl]-1,3,5-triazin-2-amine,(5)4-chloro-6-(hexahydro-1H)-azepin-1-yl)-N-[2-(4-morpholinyl)ethyl]-1,3,5-triazin-2-amine,(6)4-(hexahydro-1H-azepin-1-yl)-6-methoxy-N-[3-(4-morpholinyl)propyl-1,3,5-triazin-2-amine,and (7)N-[4-(hexahydro-1H-azepin-1-yl)thieno[3,2-d]pyrimidin-2-yl-1,4-butanediamine,or a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof.
 9. The compound according to any one of claims 1, 7 and 8,which is (1) N-(4-azepan-1-ylpyrimidin-2-yl)ethane-1,2-diamine, (2)N¹-(4-azepan-1-ylpyrimidin-2-yl)-N²,N²-dimethylethane-1,2-diamine, (3)4-azepan-1-yl-N-((3S)-1-cyclohexylpyrrolidin-3-yl)pyrimidin-2-amine, (4)4-azepan-1-yl-N-((3S)-1-benzylpyrrolidin-3-yl)pyrimidin-2-amine, (5)4-azepan-1-yl-N-((3S)-1-(2-ethylbutyl)piperidin-3-yl)pyrimidin-2-amine,(6) 4-azepan-1-yl-N-[(3S)-1-cyclohexylpiperidin-3-yl]pyrimidin-2-amine,(7)4-azepan-1-yl-N-[(3S)-1-tetrahydro-2H-pyran-4-ylpiperidin-3-yl]pyrimidin-2-amine,(8)4-(3S)-3-[(4-azepan-1-ylpyrimidin-2-yk)amino]piperidin-1-ylcyclohexanol,or (9)(3S)-N-(4-azepan-1-ylpyrimidin-2-yl)-1′-(cyclohexylcarbonyl)-1,4′-bipiperidin-3-amine.10. A pharmaceutical composition, which comprises a compound representedby formula (I):

wherein all symbols have the same meanings as those described in claim1, a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof, and a pharmaceutically acceptable carrier.
 11. Thepharmaceutical composition according to claim 10, which is a CXCR4regulating agent.
 12. The pharmaceutical composition according to claim11, wherein the CXCR4 regulating agent is a CXCR4 antagonist.
 13. Thepharmaceutical composition according to claim 12, which is a preventiveand/or therapeutic agent for human immunodeficiency virus infection. 14.The pharmaceutical composition according to claim 13, which is apreventive and/or therapeutic agent for acquired immunodeficiencysyndrome.
 15. The pharmaceutical composition according to claim 10,which is an agent for regeneration medicine.
 16. The pharmaceuticalcomposition according to claim 15, wherein the agent for regenerationmedicine is an agent for transplantation medicine.
 17. A CXCR4regulating agent, which comprises a compound represented by formula(II):

wherein T represents

wherein R¹⁰¹ and R¹⁰² each independently represents hydrogen or ahydrocarbon group which may have a substituent(s); ring A has the samemeaning as that described in claim 1; and other symbols have the samemeanings as those described in claim 1, a salt thereof, an N-oxidethereof, a solvate thereof, or a prodrug thereof, as an activeingredient, and a pharmaceutically acceptable carrier.
 18. The agentaccording to claim 17, wherein the CXCR4 regulating agent is a CXCR4antagonist.
 19. A CXCR4 regulating agent, which comprises a compoundrepresented by formula (I-3)

wherein ring A² represents a 4- to 15-membered monocyclic, bicyclic ortricyclic heterocyclic group which contains at least one nitrogen atomand may further contain 1 to 3 nitrogen atoms, 1 or 2 oxygen atomsand/or one sulfur atom; ring B² represents a 5- to 15-memberedmonocyclic, bicyclic or tricyclic heterocyclic group which contains atleast one nitrogen atom and may further contain 1 to 3 nitrogen atoms, 1or 2 oxygen atoms and/or one sulfur atom; ring A² may be substitutedwith 1 to 5 of R^(a); ring B² may be substituted with 1 to 5 of R^(b);and R^(a), R^(b) and other symbols have the same meanings as thosedescribed in claim 7, a salt thereof, an N-oxide thereof, a solvatethereof, or a prodrug thereof, as an active ingredient, and apharmaceutically acceptable carrier.
 20. The CXCR4 regulating agentaccording to claim 19, which is a CXCR4 antagonist.
 21. A CXCR4regulating agent, which comprises the compound represented by formula(I-A) according to claim 7, a salt thereof, an N-oxide thereof, asolvate thereof, or a prodrug thereof, as an active ingredient, and apharmaceutically acceptable carrier.
 22. The CXCR4 regulating agentaccording to claim 21, which is a CXCR4 antagonist.
 23. A CXCR4regulating agent, which comprises the compound represented by formula(I-B) according to claim 8, a salt thereof, an N-oxide thereof, asolvate thereof, or a prodrug thereof, as an active ingredient.
 24. TheCXCR4 regulating agent according to claim 23, which is a CXCR4antagonist.
 25. The CXCR4 regulating agent according to claim 17 or 19,which is a preventive and/or therapeutic agent for inflammatory/immunediseases, allergic diseases, infectious diseases, HIV infection ordiseases accompanied therewith, psychoneurotic diseases, cerebraldiseases, cardiovascular diseases, metabolic diseases and cancerousdiseases.
 26. The CXCR4 regulating agent according to claim 25, which isa preventive and/or therapeutic agent for HIV infection or diseasesaccompanied therewith.
 27. The CXCR4 regulating agent according to claim17 or 19, which is useful for regeneration medicine.
 28. A medicamentwhich comprises the compound according to any one of claims 1, 7, 8 and17, a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof, in combination with one or at least two of a reversetransferase inhibitor, a protease inhibitor, a CCR2 antagonist, a CCR3antagonist, a CCR4 antagonist, a CCR5 antagonist, a fusion inhibitor, anantibody against a surface antigen of HIV-1, and a vaccine of HIV-1. 29.The medicament according to claim 28, wherein the reverse transferaseinhibitor is one or at least two selected from zidovudine, didanosine,zalcitabine, stavudine, lamivudine, abacavir, adefovir, dipivoxil,emtricitabine, tenofovir, nevirapine, nevirapine, efavirenz andcapravirine.
 30. The medicament according to claim 28, wherein theprotease inhibitor is one or at least two selected from indinavir,ritonavir, nelfinavir, saquinavir, amprenavir, lopinavir and lopinavir.31. A method for antagonizing CXCR4 in a mammal, which comprisesadministering to a mammal an effective amount of a compound representedby formula (II):

wherein all symbols have the same meanings as those described in claim 1or 17, a salt thereof, an N-oxide thereof, a solvate thereof, or aprodrug thereof,
 32. A method for preventing and/or treating humanimmunodeficiency virus infection, which comprises administering to asubject in need thereof an effective amount of a compound represented byformula (I):

wherein all symbols have the same meanings as those described in claim1, a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrugthereof.
 33. A method for preventing and/or treating inflammatory/immunediseases, allergic diseases, infectious diseases, HIV infection ordiseases accompanied therewith, psychoneurotic diseases, cerebraldiseases, cardiovascular diseases, metabolic diseases and cancerousdiseases, which comprises administering to a subject in need thereof aneffective amount of the CXCR4 regulating agent according to claim 17 or19.